Phenyl acetate [C8H8O2]

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238 reactions in Reaxys

2018-05-09 18h:34m:35s (UTC)

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O

O

O

O

O

HO

Rx-ID: 572409 View in Reaxys 1/238 Yield 100 %

Conditions & References With pyridine, aluminum oxide, Time= 2h, T= 103 - 105 °C , microwave irradiation Paul, Satya; Nanda, Puja; Gupta, Rajive; Loupy, Andre; Tetrahedron Letters; vol. 43; nb. 23; (2002); p. 4261 - 4265 View in Reaxys

100 %

With 2,6-di-tert-butyl-pyridine, sodium tetracarbonyl cobaltate in acetonitrile, Time= 12h Wack, Harald; Drury III, William J.; Taggi, Andrew E.; Ferraris, Dana; Lectka, Thomas; Organic Letters; vol. 1; nb. 12; (1999); p. 1985 - 1988 View in Reaxys

100 %

With SBA-15-Ph-Pr-SO3H, Time= 0.25h, T= 20 °C Zareyee, Daryoush; Ghadikolaee, Abdollah Razaghi; Khalilzadeh, Mohammad A.; Canadian Journal of Chemistry; vol. 90; nb. 5; (2012); p. 464 - 468 View in Reaxys

99 %

With tin(IV) tetraphenylporphyrin perchlorate, Time= 0.0833333h, T= 20 °C Tangestaninejad, Shahram; Habibi, Mohammad Hossein; Mirkhani, Valiollah; Moghadam, Majid; Synthetic Communications; vol. 32; nb. 9; (2002); p. 1337 - 1343 View in Reaxys

99 %

With sodium hydroxide, Time= 0.0166667h, microwave irradiation Rajabi, Fatemeh; Saidi, Mohammad R.; Synthetic Communications; vol. 35; nb. 3; (2005); p. 483 - 491 View in Reaxys

99 %

With iodine, Time= 0.0166667h, T= 25 °C Phukan, Prodeep; Tetrahedron Letters; vol. 45; nb. 24; (2004); p. 4785 - 4787 View in Reaxys

99 %

With erbium(III) chloride, Time= 1.2h, T= 50 °C Dalpozzo, Renato; De Nino, Antonio; Maiuolo, Loredana; Oliverio, Manuela; Procopio, Antonio; Russo, Beatrice; Tocci, Amedeo; Australian Journal of Chemistry; vol. 60; nb. 1; (2007); p. 75 - 79 View in Reaxys

99 %

With thalium(III) chloride tetrahydrate, Time= 0.0333333h, T= 20 °C Kadam, Santosh T.; Kim, Sung Soo; Synthesis; nb. 20; (2008); p. 3307 - 3313 View in Reaxys

99 %

With N,N'-diiodo-N,N'-1,2-ethanediylbis(p-toluenesulphonamide), Time= 0.0333333h, T= 80 °C , neat (no solvent) Ghorbani-Vaghei, Ramin; Toghraei-Semiromi, Zahra; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 185; nb. 8; (2010); p. 1701 - 1707 View in Reaxys

99 %

With silica gel, Time= 0.0333333h, Microwave irradiation, neat (no solvent) Veisi, Hojat; Ghorbani-Vaghei, Ramin; Eskandari, Hosna; Hemmati, Saba; Rezaei, Ardashir; Hajinazari, Somaye; Far, Mohammad Raoof Heidari; Entezari, Azam; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 186; nb. 2; (2011); p. 213 - 219 View in Reaxys

99 %

With lithium bis(perfluorooctylsulfonyl)amide, Time= 38h, T= 40 °C , Catalytic behavior, Time, Reagent/catalyst Li, Guilong; Zhao, Gang; Synthetic Communications; vol. 43; nb. 1; (2013); p. 34 - 43,10

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View in Reaxys 99 %

With 4-(dimethylamino)pyridine hydrochloride in toluene, Time= 10h, T= 25 °C Liu, Zhihui; Ma, Qiaoqiao; Liu, Yuxiu; Wang, Qingmin; Organic Letters; vol. 16; nb. 1; (2014); p. 236 - 239 View in Reaxys

99 %

With pyridine, Time= 1h, T= 20 °C , Inert atmosphere Álvarez-Calero, José María; Jorge, Zacarías D.; Massanet, Guillermo M.; Organic Letters; vol. 18; nb. 24; (2016); p. 6344 6347 View in Reaxys

98 %

With aminosulfonic acid in dichloromethane, Time= 2h, T= 20 °C , Acetylation Jin, Tong-Shou; Ma, Van-Ran; Zhang, Zhan-Hui; Li, Tong-Shuang; Synthetic Communications; vol. 28; nb. 17; (1998); p.

3173 - 3177 View in Reaxys

98 %

With bismuth(lll) trifluoromethanesulfonate in acetonitrile, Time= 0.0833333h, T= 20 °C Mohammadpoor-Baltork, Iraj; Aliyan, Hamid; Reza Khosropour, Ahmad; Tetrahedron; vol. 57; nb. 27; (2001); p. 5851 5854 View in Reaxys

98 %

With H-Y zeolite, Time= 3h, T= 20 °C Heravi; Bolourtchian; Nakhshab; Zadmard; Phosphorus, Sulfur and Silicon and Related Elements; vol. 177; nb. 10; (2002); p. 2295 - 2297 View in Reaxys

98 %

With cerium triflate in acetonitrile, Time= 2.5h, T= 20 °C Dalpozzo, Renato; De Nino, Antonio; Maiuolo, Loredana; Procopio, Antonio; Nardi, Monica; Bartoli, Giuseppe; Romeo, Roberto; Tetrahedron Letters; vol. 44; nb. 30; (2003); p. 5621 - 5624 View in Reaxys

98 %

With SiO2-supported Co(II) Salen complex catalyst, Time= 1h, T= 50 °C Rajabi, Fatemeh; Tetrahedron Letters; vol. 50; nb. 4; (2009); p. 395 - 397 View in Reaxys

98 %

With Cp2Ti(OSO2C8F17)2, Time= 1h, T= 20 °C , Neat (no solvent) Qiu, Renhua; Zhang, Guoping; Ren, Xiaofang; Xu, Xinhua; Yang, Ronghua; Luo, Shenglian; Yin, Shuangfeng; Journal of Organometallic Chemistry; vol. 695; nb. 8; (2010); p. 1182 - 1188 View in Reaxys

98 %

With Methylenediphosphonic acid, Time= 2h, T= 20 °C , neat (no solvent) Xie, Minhao; Wang, Hongyong; Wu, Jun; He, Yongjun; Liu, Yaling; Zou, Pei; Journal of the Chilean Chemical Society; vol.

56; nb. 4; (2011); p. 884 - 886 View in Reaxys

98 %

General procedure: In a typical experimental procedure, to a mixture of alcohol/phenol (1mmol) and acetic anhydride (1.0mmol) or acyl chloride (1.0mmol) in dichloromethane solvent (2vol) or without solvent, Zn(OTf)2 (0.1molpercent) was added. The reaction mixture was stirred at room temperature for the specified time. Completion of reaction was monitored by TLC, after quenching with a saturated solution of NaHCO3 and the products were extracted in to dichloromethane (3×10mL). The combined organic layer was washed with water, dried over anhydrous Na2SO4, and concentrated in vacuum to obtain the product.

With zinc trifluoromethanesulfonate, Time= 0.00277778h, T= 20 °C , Solvent, Reagent/catalyst Kumar, N. Uday; Reddy, B. Sudhakar; Reddy, V. Prabhakar; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 55; nb. 4; (2014); p. 910 - 912 View in Reaxys

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98 %

With vitamin B1 supported on silica-encapsulated γ-Fe2O3 nanoparticles in neat (no solvent), Time= 1h, T= 20 °C , Green chemistry Azizi, Kobra; Heydari, Akbar; RSC Advances; vol. 4; nb. 17; (2014); p. 8812 - 8816 View in Reaxys

98 %

General procedure for Acetylation General procedure: In a typical experimentalprocedure, to a mixture of alcohol/phenol (1 mmol) and acetic anhydride (1.0mmol) in dichloromethane solvent (2 vol)/without solvent, Zn(OTf)2(0.01-0.1 mol percent) was added. The reaction mixture was stirred at roomtemperature for the appropriate amount of time. Completion of reaction wasmonitored by TLC after quenching with a saturated solution of NaHCO3and the products were extracted in to dichloromethane (3 X 10.0 mL). Thecombined organic layer was washed with water, dried over anhydrous Na2SO4and concentrated under reduced pressure. All products were characterized bycomparison of their spectral data and physical prosperities with those ofauthentic samples.

With zinc trifluoromethanesulfonate in dichloromethane, Time= 0.00277778h, T= 25 °C Uday Kumar; Sudhakar Reddy; Prabhakar Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 55; nb. 4; (2014); p.

910 - 912 View in Reaxys

98 %

MW-Assisted, (4)-Catalyzed Acetylation of Alcohols General procedure: A mixture of molecular 4 (1.0×10-2mmol Gd), alcohol (2.0 mmol for liquid substrate and 0.5 mmol for solid substrate), and acetic anhydride (1.5 mmol for liquid substrate and 5 mmol for solid substrate) in DMF (400 µL) was placed in the reaction vessel under 300 W MW for 60 s. After the reaction, the resulting mixture was used directly for 1H NMR analysis for the analytic yield.

With [Gd(1,4,7,10-tetraazacyclododecane-1,4,7-triacetate)] in N,N-dimethyl-formamide, Time= 0.0166667h, Microwave irradiation, Catalytic behavior, Reagent/catalyst Chang, Tsao-Ching; Yu, Shuchun Joyce; Synthetic Communications; vol. 45; nb. 5; (2015); p. 661 - 672 View in Reaxys

97 %

With In(OSO2CF3)3 in acetonitrile, Time= 0.25h, T= 20 °C , Acetylation Chauhan, Kamlesh K.; Frost, Christopher G.; Love, Ian; Waite, David; Synlett; nb. 11; (1999); p. 1743 - 1744 View in Reaxys

97 %

With yttria-stabilized zirconia in acetonitrile, Time= 12h, Heating Kumar; Pandey; Bodas; Dongare; Synlett; nb. 2; (2001); p. 206 - 209 View in Reaxys

97 %

With K5CoIIIW12O40 in acetonitrile, Time= 0.25h, T= 20 °C Habibi, Mohammad H.; Tangestaninejad, Shahram; Mirkhani, Valiollah; Yadollahi, Bahram; Monatshefte fur Chemie; vol. 133; nb. 3; (2002); p. 323 - 327 View in Reaxys

97 %

With copper(II) bis(tetrafluoroborate), Time= 0.5h, T= 20 °C Chakraborti, Asit K.; Gulhane, Rajesh; Shivani; Synthesis; nb. 1; (2004); p. 111 - 115 View in Reaxys

97 %

With Sulfate, titanium(IV) oxide in dichloromethane, Time= 0.0666667h, T= 40 °C Ma, Yan-Ran; Jin, Tong-Shou; Wang, Zhen-Hua; Li, Tong-Shuang; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 42; nb. 7; (2003); p. 1777 - 1778 View in Reaxys

97 %

With H3[P(Mo3O10)4]*nH2O, Time= 0.166667h, T= 20 °C Kadam, Santosh T.; Sung, Soo Kim; Synthesis; nb. 2; (2008); p. 267 - 271 View in Reaxys

97 %

Typical procedure: Acetylation of methyl α-d-glucopyranoside.

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General procedure: DABCO (1.0 mol equiv) was added to a suspension of the sugar (10.0 g, 51.5 mmol) in Ac2O (1.2 mol equiv per OH group) and the mixture was stirred at rt. After completion of the reaction (TLC, eluent, EtOAc:n-Hex, 2:3) the mixture was poured onto crushed ice and was stirred for a few min when precipitation of the desired methyl 2,3,4,6-tetra-O-acetyl-γ-dglucopyranoside took place along with dissolution of DABCO in water (the latter indicated by TLC and viewing the spot in an iodine chamber). The product was isolated by filtration at the pump followed by washing with ice-cold water and drying. It was pure enough for direct further use. Yield, 18.3 g, 98percent. An analytically pure sample was obtained by recrystallization from 95percent ethanol.It may be noted that addition of DABCO and stirring lead to warming up of the reaction mixture. In reactions carried out on 10-20 g scale this is advantageous in that considerable rate enhancement can be obtained in such cases. However in reactions on a much larger scale (50-100 g and above) the addition of DABCO should preferably be carried out portion-wise to keep the reaction mixture from getting over heated.

With 1,4-diaza-bicyclo[2.2.2]octane, Time= 0.5h, T= 20 °C , Neat (no solvent) Ch, Ratnasekhar; Tyagi, Mohit; Patil, Premanand Ramrao; Kartha, K.P. Ravindranathan; Tetrahedron Letters; vol. 52; nb. 44; (2011); p. 5841 - 5846 View in Reaxys 97 %

With N-methyl-N-[2-(prop-2-yn-1-yloxy)ethyl]pyridin-4-amine functionalised microporous organic nanotube network in dichloromethane, Time= 1h, T= 20 °C , Catalytic behavior Yu, Wei; Zhou, Minghong; Wang, Tianqi; He, Zidong; Shi, Buyin; Xu, Yang; Huang, Kun; Organic Letters; vol. 19; nb. 21; (2017); p. 5776 - 5779 View in Reaxys

96 %

With nickel dichloride, Time= 0.166667h, microwave irradiation Constantinou-Kokotou, Violetta; Peristeraki, Anna; Synthetic Communications; vol. 34; nb. 22; (2004); p. 4227 - 4232 View in Reaxys

96 %

With aluminum triflate, Time= 0.00416667h, T= 20 °C Kamal, Ahmed; Khan, M. Naseer A.; Reddy, K. Srinivasa; Srikanth; Krishnaji; Tetrahedron Letters; vol. 48; nb. 22; (2007); p. 3813 - 3818 View in Reaxys

96 %

With cadmium(II) oxide, Time= 0.166667h, T= 80 °C , Neat (no solvent), Microwave irradiation Mazaheritehrani; Asghari; Orimi, R. Lotfi; Pahlavan; Asian Journal of Chemistry; vol. 22; nb. 4; (2010); p. 2554 - 2564 View in Reaxys

96 %

With N-methylmorpholinium propanesulfonic acid ammonium hydrogensulfate, Time= 0.0333333h, T= 25 °C , Inert atmosphere, neat (no solvent), chemoselective reaction Yue, Caibo; Liu, Qingqing; Yi, Tingfeng; Chen, Yun; Monatshefte fur Chemie; vol. 141; nb. 9; (2010); p. 975 - 978 View in Reaxys

96 %

With [SnIV(TNH2PP)(OTf)2]*CMP in acetonitrile, Time= 0.133333h, T= 20 °C Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Mohammadpoor-Baltork, Iraj; Gharaati, Shadab; Comptes Rendus Chimie; vol. 14; nb. 12; (2011); p. 1080 - 1087 View in Reaxys

96 %

With (2,3,4,5,6-pentafluorophenyl)ammonium triflate in neat (no solvent), Time= 0.666667h, T= 20 °C Khaksar, Samad; Zakeri, Hasan; Combinatorial Chemistry and High Throughput Screening; vol. 15; nb. 7; (2012); p. 576 579,4 View in Reaxys

96 %

With silica-supported boric acid in neat (no solvent), Time= 1h, T= 50 °C Kumar, Vishal; Singh, Chitra; Sharma, Upendra; Verma, Praveen K.; Singh, Bikram; Kumar, Neeraj; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 53; nb. 1; (2014); p. 83 - 89 View in Reaxys

96 %

Acetylation of Alcohols, Phenols, Thiols, and Amines

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General procedure: A mixture of the substrate (1 mmol), acetic anhydride (3 mmol), and RiHA (0.3 g)was stirred at room temperature and/or 80 °C. After completion of the reaction (TLC), the reaction mixture was triturated with EtOAc (15 mL) and the reagent was filtered. The organic layer was washed with saturated NaHCO3 and water (3×15 mL), and dried over anhydrous MgSO4. Evaporation of the solvent under reduced pressure gave the requested products in good to high yields.

With rice husk ash, Time= 0.0833333h, T= 80 °C , Green chemistry Shirini; Akbari-Dadamahaleh, Somayeh; Mohammad-Khah, Ali; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 189; nb. 5; (2014); p. 577 - 586 View in Reaxys 96 %

in neat (no solvent), Time= 0.166667h, Microwave irradiation Zhang, Yu-Quan; Li, Yan-Chun; Zhu, Ji-Hua; Li, Zhi-Feng; Guo, Guo-Zhe; Chen, Dong-Ping; Asian Journal of Chemistry; vol. 26; nb. 22; (2014); p. 7746 - 7748 View in Reaxys

96 %

With 2,3-dihydro-5,7-bismethyl-1,4-diazepine monohydroperchlorate in neat (no solvent), Time= 3h, T= 40 °C Giri, Santosh Kumar; Gour, Rajesh; Kartha, K. P. Ravindranathan; RSC Advances; vol. 7; nb. 22; (2017); p. 13653 13667 View in Reaxys

95 %

With carbon in dichloromethane, Time= 1h, T= 20 °C , Acetylation Jin, Tong-Shou; Ma, Yan-Ran; Li, Tong-Shuang; Zhang, Zhan-Hui; Duan, Guang-Bo; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 1; (1999); p. 109 - 110 View in Reaxys

95 %

With zirconium sulfophenyl phosphonate in dichloromethane, Time= 4h, T= 20 °C , Acetylation Curini, Massimo; Epifano, Francesco; Marcotullio, Maria Carla; Rosati, Ornelio; Rossi, Monia; Synthetic Communications; vol. 30; nb. 7; (2000); p. 1319 - 1329 View in Reaxys

95 %

With phosphorus pentoxide, silica gel, Time= 0.333333h, T= 20 °C Eshghi, Hossein; Shafieyoon, Parvaneh; Journal of Chemical Research; nb. 12; (2004); p. 802 - 805 View in Reaxys

95 %

With nickel dichloride, Time= 0.5h, T= 20 °C , Neat (no solvent) Meshram, Gangadhar; Patil, Vishvanath D.; Synthetic Communications; vol. 39; nb. 24; (2009); p. 4384 - 4395 View in Reaxys

95 %

With alumina supported P2O5, Time= 0.333333h, T= 20 °C , neat (no solvent) Zarei, Amin; Hajipour, Abdol R.; Khazdooz, Leila; Synthetic Communications; vol. 41; nb. 12; (2011); p. 1772 - 1785 View in Reaxys

95 %

With sulfuric acid supported on poly(4-vinylpyridine) (P4VP) in dichloromethane, Time= 1h, T= 20 °C Borah, Kalyan Jyoti; Dutta, Papia; Borah, Ruli; Bulletin of the Korean Chemical Society; vol. 32; nb. 1; (2011); p. 225 - 228 View in Reaxys

95 %

With silica-sulfuric acid nanoparticles in neat (no solvent), Time= 0.166667h, T= 20 °C Salavati-Niasari, Masoud; Javidi, Jaber; Combinatorial Chemistry and High Throughput Screening; vol. 15; nb. 9; (2012); p.

705 - 712 View in Reaxys

95 %

In a typical procedure for the conversion of a 4-ethylphenol into a 4-ethylphenyl acetate General procedure: 4-ethylphenol (1 mmol, 0.122 g) was added to a stirred solution of imidazole (0.08 mmol 0.005 g) and acetic anhydride (2.0 mmol, 0.188 mL) at ambient temperature, and the progress of the reaction was monitored by TLC. Upon completion of the reaction (2.5 h), the crude procuct mixture was purified by column chromatography on silica gel, using n-hexane/ ethyl acetate (10:1) as the eluent, to give 4-ethylphenyl acetate as colorless liquid (0.143 g, 87percent yield). 1H NMR (400

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MHz, CDCl3): γ 1.31 (t, J=7.6 Hz 3H), 2.33 (s, 3H), 2.71 (q, J=7.6 Hz, 2H) 7.07 (d, J=8.4 Hz, 2H)7.27 (d, J=8.4 Hz, 2H). 13C (100 MHz, CDCl3): γ 15.6, 21.1, 28.3, 121.3, 128.8, 141.7, 148.7, 169.7.

With 1H-imidazole, Time= 2.5h, T= 20 °C , Green chemistry Nowrouzi, Najmeh; Alizadeh, Seyedeh Zahra; Chinese Journal of Catalysis; vol. 34; nb. 9; (2013); p. 1787 - 1790 View in Reaxys 95 %

2.7. Acylation of alcohols General procedure: The alcohol (1.5 mmol) and anhydride (3 mmol) were mixed in a 50 mL Schlenk tube, and then TPB-DMAP or TPA-DMAP (0.045 mmol) was added. The mixture was stirred at room temperature unless otherwise indicated. After completion of the reaction, the reaction mixture was subjected to centrifugation and the solid catalyst was separated. The liquid phase was harvested by decanting and evaporated, and the residue was purified by column chromatography on silica gel to afford the pure ester product. For recycling the catalyst, the isolated catalyst was washedwith diethyl ether and dried in vacuum, the recovered yellow solid was reused directly for the next run.

With 4-(N,N-dimethylamino)pyridine based 1,3,5,7-tetraphenyladamantane polymer in neat (no solvent), Time= 1h, T= 25 °C , Schlenk technique Xu, Wei; Xia, Wu; Guan, Yukun; Wang, Yiming; Lu, Cuifen; Yang, Guichun; Nie, Junqi; Chen, Zuxing; Reactive and Functional Polymers; vol. 104; (2016); p. 15 - 21 View in Reaxys

95 %

Synthesis of phenyl acetate 2a A mixture of phenol (1a) (9.4 gm, 0.1 mol) and dry pyridine (5 mL) was placed in a 500 mL beaker. It was kept in ice bath and acetic anhydride (12.75 mL, 0.125 mol) was added slowly with constant stirring for 4 to 5 hr. The reaction mixture was poured on a mixture of ice cold water and concentrated hydrochloric acid (10 mL) and extracted with ethylacetate (2×50 mL). The extract was washed successively with water, 10percent NaOH solution and brine solution (2×20 mL). It was dried over anhydrous sodium sulphate. The solvent was removed by distillation and phenyl acetate was collected at 195 to 197 °C, Yield 95 percent.

With pyridine, Cooling with ice Shaikh, Mubarak H.; Subhedar, Dnyaneshwar D.; Khedkar, Vijay M.; Jha, Prakash C.; Khan, Firoz A. Kalam; Sangshetti, Jaiprakash N.; Shingate, Bapurao B.; Chinese Chemical Letters; vol. 27; nb. 7; (2016); p. 1058 - 1063 View in Reaxys

95 %

With tetrakis(triphenylphosphineoxide)dioxouranium(VI) perchlorate in dichloromethane-d2, Time= 2h, T= 22 °C Takao, Koichiro; Akashi, Shin; RSC Advances; vol. 7; nb. 20; (2017); p. 12201 - 12207 View in Reaxys

95.3 %

3.1 : Esterification reaction In a 500 ml reaction flask,62.2 g (0.66 mol) of phenol and 70.8 g (0.69 mol) of acetic anhydride were added,After stirring, the mixture was cooled to 5 ° C,Dropping the first drop of concentrated sulfuric acid,To be reduced to room temperature after the reaction and then drop the second drop of concentrated sulfuric acid,Twice the amount of concentrated sulfuric acid dosage of 0.5g;After the dripping of concentrated sulfuric acid,Heated to reflux 60min,Cooling to 60 ~ 70 , after vacuum distillation of acetic acid,The reaction solution was poured into twice the amount of water,With alkali 5percent sodium hydroxide to adjust the pH to 8 ~ 9,Extracted three times with ethyl acetate,Combined extract,Dried over anhydrous magnesium sulfate,filter,concentrategetPhenyl acetateliquidBody 84.6g,Yield 95percent; divided into three spare With sulfuric acid, Time= 1.16667h, T= 5 °C , Reflux, Concentration, Temperature Patent; Zunyi Teachers College; Huang, Chibao; (7 pag.); CN106167449; (2016); (A) Chinese View in Reaxys

95 %

Phenyl Acetate; Typical Procedure Ac2O (0.6 mL, 6 mmol) was added to a mixture of phenol (0.47 g, 5mmol), and K2CO3 (1.35 g, 10 mmol) in CH2Cl2 (25 mL).

The mixture was stirred for 24 h at r.t. The resulting mixture was washed several times with H2O. The organic phase was dried (anhyd Na2SO4) and then evaporated under reduced pressure. Pure phenyl acetate was obtained in 95percent yield (120 mg) after column chromatography.

With potassium carbonate in dichloromethane, Time= 24h, T= 20 °C Rostami, Abed; Rostami, Amin; Ghaderi, Arash; Gholinejad, Mohammad; Gheisarzadeh, Sajedeh; Synthesis (Germany); vol. 49; nb. 22; (2017); p. 5025 - 5038; Art.No: SS-2016-N0842-OP

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View in Reaxys 94.5 %

With ZSM-35 zeolite in acetonitrile, Time= 2.5h, Heating Srivastava; Venkatathri; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 43; nb. 4; (2004); p.

888 - 891 View in Reaxys

94 %

With [{CpHf(OH2)3}2(μ2-OH)2][OSO2C8F17]4*4H20*2THF, Time= 2h, T= 20 °C Qiu, Renhua; Zhang, Guoping; Zhu, Yuyang; Xu, Xinhua; Shao, Lingling; Li, Yinhui; An, Delie; Yin, Shuangfeng; Chemistry - A European Journal; vol. 15; nb. 26; (2009); p. 6488 - 6494 View in Reaxys

94 %

2.2. General experimental procedure for acetylation of alcohols and phenols with Ac2O catalyzed by PS/GaCl3 complex General procedure: To a solution of alcohol or phenol (1 mmol) and Ac2O (1.1–1.3 mmol) in methylene chloride (5 mL) was added PS/GaCl3 (0.1 mmol) and the resulting mixture was stirred at room temperature. The progress of the reaction was monitored by TLC and GLC. After completion of the reaction, the catalyst was filtered off and washed with methylene chloride (2*10 mL) and the filtrate concentrated on a rotary evaporator under reduced pressure to afford the crude acetate product. Further purification was achieved by column chromatography on silica gel (Merck, 100–200 mesh, hexane-EtOAC, 90/10, v/v). The spent polymeric catalyst from different experiments was combined, washed with ether and dried overnight in a vacuum oven and reused.

With polystyrene-supported gallium trichloride#10; in dichloromethane, Time= 0.833333h, T= 20 °C Rahmatpour, Ali; Comptes Rendus Chimie; vol. 15; nb. 11-12; (2012); p. 1048 - 1054 View in Reaxys

94 %

With poly(N-vinylimidazole) in neat (no solvent), Time= 0.3h, T= 20 °C , Green chemistry Khaligh, Nader Ghaffari; RSC Advances; vol. 3; nb. 1; (2013); p. 99 - 110 View in Reaxys

94 %

With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate in neat (no solvent), Time= 0.75h, T= 50 °C , Green chemistry Ji, Li; Qian, Chao; Chen, Xin-Zhi; Monatshefte fur Chemie; vol. 144; nb. 3; (2013); p. 369 - 374 View in Reaxys

94 %

2.3. Acetylation of alcohols, phenols, thiols, and amines with different substrates General procedure: A mixture of 1 mmol substrate, 2–3 mmol acetic anhydride, and 5 mg SuSA (0.028 mmol) was stirred at room temperature in the absence of a solvent. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was diluted with 15 ml ethyl acetate and filtered. Then the solid residue was washed with 5 ml ethyl acetate, then 5 ml acetone and then dried. The recovered catalyst could be used for three more reaction runs. The organic layer was washed with 5 ml of a saturated solution of NaHCO3, 20 ml brine and 20 ml water, and dried over MgSO4. Evaporation of the solvent followed by column chromatography on silica gel followed by evaporation of the solvent gave the desired product in good to high yields.

With succinimide-N-sulfonic acid in neat (no solvent), Time= 0.166667h, T= 20 °C , Mechanism Shirini, Farhad; Khaligh, Nader Ghaffari; Chinese Journal of Catalysis; vol. 34; nb. 4; (2013); p. 695 - 703 View in Reaxys

94 %

2.4. General procedure for acetylation with Ac2O catalyzed byRHA/TiO2(30percent) General procedure: 1 mmol of the substrate (alcohol, phenol or amine) wasadded to a mixture of RHA/TiO2(30percent) (20 mg) and aceticanhydride (1.5 mmol per OH/NH2 group) and the resulting mixture was stirred at room temperature. After completionof the reaction (mentioned by TLC), dichloromethane(20 mL) was added and the catalyst was separated byfiltration. The organic phase was washed with 10percent aqueoussolution of sodium bicarbonate (2 20 mL) and dried overNa2SO4. The solvent was removed under reduced pressureto afford the desired product in good to high yields. Thespectral (IR, 1H and 13C NMR) data of new compounds arepresented below: With rice husk ash/TiO2 nanocomposite in neat (no solvent), Time= 0.2h, T= 20 °C , Green chemistry Seddighi, Mohadeseh; Shirini, Farhad; Goli-Jolodar, Omid; Comptes Rendus Chimie; vol. 19; nb. 8; (2016); p. 1003 - 1010 View in Reaxys

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93 %

With [n-Bu2Sn(H2O)4][C6H5SO3]2, Time= 2.5h, T= 20 °C Chandrasekhar, Vadapalli; Boomishankar, Ramamoorthy; Gopal, Kandasamy; Sasikumar, Palani; Singh, Puja; Steiner, Alexander; Zacchini, Stefano; European Journal of Inorganic Chemistry; nb. 20; (2006); p. 4129 - 4136 View in Reaxys

93 %

General procedure for the acetylation of alcohols and phenols with Ac2O catalyzed by GO. General procedure: To a solution of alcohols or phenols (3 mmol) and Ac2O (4.5 mmol; 9 mmol for dihydroxybenzenes) in CH3CN or CH2Cl2(2 mL) in a round-bottom flask was added GO (5 wtpercent of alcohols orphenols). The mixture was stirred at 20 °C and the progress of the reaction was monitored by thin layer chromatography (TLC) analysis. After the completion of the reaction, the catalyst was filtered and washed with ethyl acetate (20 mL x 2). The filtrate was combined and washed with 15 mL of saturated sodium carbonate. The organic phase was dried over Na2SO4 and evaporated in vacuo to obtain the desired products. To determine the catalytic activity of Mn and K, we added MnO2, MnSO4 or KCl in the reaction between2-phenylethanol with Ac2O instead of GO and the yields of the corresponding ester (determined by 1H NMR) were listed in Table S1.

With graphite oxide in dichloromethane, Time= 0.133333h, T= 20 °C , Green chemistry Liu, Yuan-Yuan; Qi, Jun-Mei; Bai, Li-Sha; Xu, Yue-Long; Ma, Ning; Sun, Fei-Fei; Chinese Chemical Letters; vol. 27; nb.

5; (2016); p. 726 - 730 View in Reaxys

92 %

With Sm{Nlt;SO2OCH(CF3)2gt;2}3 in dichloromethane, Time= 0.766667h, T= 30 °C , Acetylation Nie, Jin; Zhao, Zhongming; Xu, Jun; Liu, Dafan; Journal of Chemical Research - Part S; nb. 2; (1999); p. 160 - 161 View in Reaxys

92 %

With silica-bonded N-propyl sulfamic acid, Time= 6h, T= 20 °C , chemoselective reaction Niknam, Khodabakhsh; Saberi, Dariush; Tetrahedron Letters; vol. 50; nb. 37; (2009); p. 5210 - 5214 View in Reaxys

92 %

With silver trifluoromethanesulfonate, Time= 0.25h, T= 60 °C , neat (no solvent) Das, Rima; Chakraborty, Debashis; Synthesis; nb. 10; (2011); p. 1621 - 1625; Art.No: Z17211SS View in Reaxys

92 %

With rice-husk-supported FeCl3 nano particles in neat (no solvent), Time= 0.8h, T= 80 °C Shirini, Farhad; Akbari-Dadamahaleh, Somayeh; Mohammad-Khah, Ali; Aliakbar, Ali-Reza; Comptes Rendus Chimie; vol. 17; nb. 2; (2014); p. 164 - 170 View in Reaxys

92 %

Typical experimental procedure: General procedure: B(C6F5)3 (0.5 mol percent) was added to a mixture of alcohol/phenol/thiophenol/amine (1 mmol) and acetic anhydride (1.2 mmol), and the reaction mixture was stirred at room temperature until the complete conversion of starting material (monitored by TLC). After completion of reaction, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 15 mL). The organic layer was washed with cold saturated sodium bicarbonate solution (2 20 mL) followed by brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure and products were purified over silica gel column chromatography in ethylacetate/hexane. All compounds were characterized and confirmed by comparison of their spectral data and physical properties with reported literature.

With tris(pentafluorophenyl)borate in neat (no solvent), Time= 0.25h, T= 20 °C , Green chemistry Prajapti, Santosh Kumar; Nagarsenkar, Atulya; Babu, Bathini Nagendra; Tetrahedron Letters; vol. 55; nb. 10; (2014); p.

1784 - 1787 View in Reaxys

92 %

General experimental procedure for the acetylation of substrates under solvent-free conditions General procedure: ZPFe (1 molpercent) was added to a mixture of alcohol (1 mmol) and AA (2 mmol), and the resulting mixture was stirred at 40 °C for a specified time (Scheme 2). Upon completion of the reaction (as determined by gas chromatography), the catalyst was separated from the reaction mixture by centrifuge, after which the supernatant was collected and diluted with a 10percent NaHCO3 solution (10 mL) before being extracted with Et2O (2 × 10 mL).The combined organic extracts were washed and then dried over anhydrous CaCl2 before being evaporated to dryness under vacuum to give the desired product. In

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some cases, it was necessary to purify the product by column chromatography ona silica gel column with elution by a mixture of cyclohexane and ethyl acetate.

With ziconium(IV) oxychloride octahydrate in neat (no solvent), Time= 0.25h, T= 40 °C , Green chemistry, Reagent/catalyst Hajipour, Abdol R.; Karimi, Hirbod; Masti, Amir; Chinese Journal of Catalysis; vol. 36; nb. 4; (2015); p. 595 - 602 View in Reaxys 92 %

General procedure for the acetyl protection reactions General procedure: A mixture of the substrate (1 mmol), acetic anhydride(1 mmol) and PC–NPs (12 mg) was stirred at room temperature. After completion of the reaction (monitored by TLC using a 1:1 mixture of EtOAc/n-hexane), EtOAc (15 mL)was added and the catalyst was filtered. The organic layer was washed with saturated solution of NaHCO3 and water(3 × 15 mL), and dried over anhydrous MgSO4. Evaporation of the solvent under reduced pressure gave the requested acetates in high purity.

With poly(4-vinylpyridine) supported copper(II) oxide nanoparticles in neat (no solvent), Time= 0.0333333h, T= 20 °C , chemoselective reaction Shirini, Farhad; Fallah-Shojaei, Abdollah; Abedini, Masoumeh; Samavi, Laleh; Journal of the Iranian Chemical Society; vol. 13; nb. 9; (2016); p. 1699 - 1712 View in Reaxys

91 %

With ruthenium(III) 2,4-pentanedionate, Time= 2h, T= 25 °C Varala, Ravi; Nasreen, Aayesha; Adapa, Srinivas R.; Canadian Journal of Chemistry; vol. 85; nb. 2; (2007); p. 148 - 152 View in Reaxys

91 %

General procedure: 10 mmol of the alcohol was dissolved, under stirring, in 10 mmol (ca. 2 mL) of the corresponding ionic liquid at room temperature. Then 1.10 equiv of acetic anhydride per hydroxyl group was added to the medium and the reaction was monitored by tlc. Products were isolated either by extraction with ether and/or petroleum ether, washed with aqueous bicarbonate or by distillation under reduced pressure. Table 1 summarises results obtained for both ionic liquids and a variety of alcohols.

With 3-butyl-1-methylimidazolium acetate, Time= 0.0166667h, T= 20 °C , Ionic liquid Lopez, Ignacio; Bravo, Jose Luis; Caraballo, Manuel; Barneto, Jose Luis; Silvero, Guadalupe; Tetrahedron Letters; vol.

52; nb. 26; (2011); p. 3339 - 3341 View in Reaxys

91 %

General experimental procedure for the acetylation of substrates under solvent-free conditions General procedure: ZPNi (1 mol percent) was added to a mixture of alcohol(1 mmol) and AA (2 mmol), and the resulting mixture was stirred at 40 °C for the specified time (Scheme 2). Upon completion of the reaction (as determined by GC), the catalyst was separated from the reaction mixture by centrifuge,then the supernatant was collected and diluted with 10 percentNaHCO3 solution (10 ml) before being extracted with Et2O(2 × 10 ml). The combined organic extracts were washed and then dried over anhydrous CaCl2 before being evaporated to dryness under vacuum to give the desired product. In some cases, it was necessary for the product to be purified by column chromatography over silica gel eluting witha mixture of cyclohexane and ethyl acetate.

With nickel zirconium phosphate in neat (no solvent), Time= 0.25h, T= 40 °C , Reagent/catalyst Hajipour, Abdol Reza; Karimi, Hirbod; Kohi, Afshin; Journal of the Iranian Chemical Society; vol. 13; nb. 1; (2016); p. 55 64 View in Reaxys

90 %

With iodine, Time= 0.5h, Ambient temperature Borah, Ruli; Deka, Nabajyoti; Sarma, Jadab C.; Journal of Chemical Research - Part S; nb. 3; (1997); p. 110 - 111 View in Reaxys

90 %

With lithium chloride, Time= 3h, Ambient temperature Sabitha, Gowravaram; Subba Reddy; Srividya; Yadav; Synthetic Communications; vol. 29; nb. 13; (1999); p. 2311 - 2315 View in Reaxys

90 %

With HZSM-5 zeolite, Time= 1h, T= 50 °C , Acetylation Heravi, Majid M.; Tajbakhsh, Mahmood; Mohajerani, Bagher; Ghassemzadeh, Mitra; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 7; (1999); p. 859 - 860

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View in Reaxys 90 %

With lithium perchlorate, Time= 6h, T= 40 °C Nakae; Kusaki; Sato; Synlett; nb. 10; (2001); p. 1584 - 1586 View in Reaxys

90 %

With aluminium dodecatungsten phosphate, Time= 0.05h, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Nowrouzi, Farhad; Amani, Kamal; Chemical Communications; nb. 6; (2003); p. 764 - 765 View in Reaxys

90 %

With vanadyl sulfate trihydrate, Time= 1.5h, T= 20 °C Oskooie, Hossein A.; Baghernezhad, Bita; Heravi, Majid M.; Beheshtiha; Journal of the Chinese Chemical Society; vol. 55; nb. 4; (2008); p. 713 - 715 View in Reaxys

90 %

With 1-hexyl-3-methylimidazolium hydrogen sulphate, Time= 0.25h, T= 50 °C , Neat (no solvent) Hajipour, Abdol R.; Khazdooz, Leila; Ruoho, Arnold E.; Journal of the Chinese Chemical Society; vol. 56; nb. 2; (2009); p.

398 - 403 View in Reaxys

90 %

With carbon-silica composite from starch (7.5 molpercent SO3H), Time= 3h, T= 60 °C , solvent-free conditions Gupta, Princy; Paul, Satya; Green Chemistry; vol. 13; nb. 9; (2011); p. 2365 - 2372 View in Reaxys

90 %

With decamolybdodivanadogermanic acid nanoparticles, Time= 0.366667h, T= 24.84 °C , Neat (no solvent) Farhadi, Saeid; Zareisahamieh, Reza; Zaidi, Masoumeh; Journal of the Brazilian Chemical Society; vol. 22; nb. 7; (2011); p.

1323 - 1332 View in Reaxys

90 %

General Procedure for acetylation of Alcohols, Phenols, Thiol and Amine with Ac2O in the presence of PBNS under solvent-free conditions General procedure: Alcohol, phenol, thiol or amine (1 mmol) was added to a mixture of Ac2O (2 mmol) and PBNS (30 mg), and the resulting mixture was stirred at room temperature. After completion of the reaction as monitored by TLC (nhexane/acetone: 9/1), CH2Cl2 (10 mL) was added to the reaction mixture, stirred for 1 min, and the catalyst was filtered.The precipitate was washed with CH2Cl2 (210 mL) and dried to give the recycled PBNS. Water (20 mL) was added to the filtrate and decanted. The organic layer was dried over anhydrous Na2SO4. Then, the purity of the product was checked by TLC for several times, which had only one spot related to the final product; after ensuring about that, evaporation of the solvent gave the desired pure product in good yield.

With poly(N,N'-dibromo-N-ethylnaphthyl-2,7-sulfonamide) in neat (no solvent), Time= 1.16667h, T= 20 °C Khazaei, Ardeshir; Saednia, Shahnaz; Roshani, Liela; Kazem-Rostami, Masoud; Zare, Abdolkarim; Letters in Organic Chemistry; vol. 11; nb. 3; (2014); p. 159 - 167 View in Reaxys

90 %

With multi-walled carbonnanotubes functionalized with phosphonic acid in neat (no solvent), Time= 0.833333h, T= 20 °C Dehghani, Farzaneh; Sardarian, Ali Reza; Doroodmand, Mohammad Mehdi; Journal of the Iranian Chemical Society; vol.

11; nb. 3; (2014); p. 673 - 684 View in Reaxys

90 %

2.3. General experimental procedure for the acetylation of substrates under solvent-free conditions General procedure: ZPCu (2 molpercent) was added to a mixture of phenol (1 mmol)and AA (2 mmol), and the resulting mixture was stirred at 60 °C for the specified time (Scheme 2). Upon completion of the reaction(as determined by GC), the catalyst was separated from the reaction mixture by centrifuge, then the supernatant was collected and diluted with 10percent NaHCO3 solution (10 ml) before being extracted with Et2O (2 . 10 ml). The combined organic extracts were washed and then dried over anhydrous CaCl2 before being evaporated to dryness under vacuum to give the desired product. In some cases, it was necessary for the product to be purified by column chromatography over silica gel eluting with a mixture of cyclohexane and ethyl acetate.

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With Cu(2+)*Zr(4+)*2PO4 (3-) = CuZr(PO4)2, Time= 0.5h, T= 60 °C , Concentration, Temperature, Time, Solvent Hajipour, Abdol R.; Karimi, Hirbod; Chinese Journal of Catalysis; vol. 35; nb. 12; (2014); p. 1982 - 1989 View in Reaxys 90 %

Acetylation of benzyl alcohol using aceticanhydride catalyzed by tribromoisocyanuric acid General procedure: To a mixture of the benzyl alcohol (1 mmol)and acetic anhydride (3 mmol); 0.074 gtribromoisocyanuric acid (0.2 mmol) was added. Thereaction mixture was stirred at room temperaturefor 12 min. After completion of the reaction (TLC),dichloromethane (10 mL) was added to the reactionmixture and filtered. The product was extracted withH2O (3×10 mL), and the organic layer was driedover anhydrous Na2SO4salt. Then solvent wasevaporated to dryness to afford the pure product.

With tribromo-isocyanuric acid in neat (no solvent), Time= 1.16667h, T= 20 °C Hekmatian, Zahra; Khazaei, Ardeshir; Oriental Journal of Chemistry; vol. 31; nb. 3; (2015); p. 1565 - 1570 View in Reaxys

89 %

With silica gel-supported phosphotungstic acid in dichloromethane, Time= 0.0333333h, T= 20 °C Jin, Tong-Shou; Xiao, Jin-Chong; Wang, Zhen-Hua; Li, Tong-Shuang; Journal of Chemical Research - Part S; nb. 7; (2003); p. 412 - 414 View in Reaxys

89 %

With o-benzenedisulfonimide, Time= 0.0833333h, T= 20 °C Barbero, Margherita; Cadamuro, Silvano; Dughera, Stefano; Venturello, Paolo; Synthesis; nb. 22; (2008); p. 3625 - 3632 View in Reaxys

89 %

With ruthenium trichloride, Time= 2h, T= 40 °C , Inert atmosphere, Ionic liquid Xi, Zhiwen; Hao, Wenyan; Wang, Pingping; Cai, Mingzhong; Molecules; vol. 14; nb. 9; (2009); p. 3528 - 3537 View in Reaxys

89 %

With 1-butyl-3-methylimidazolium tetrachloridoferrate(III), Time= 0.333333h, T= 20 °C , Ionic liquid Wanga, Dong-Sheng; Lib, Gui-Yun; Pengb, Yan-Qing; Journal of the Chinese Chemical Society; vol. 56; nb. 4; (2009); p.

834 - 838 View in Reaxys

89 %

With zirconium phosphate in neat (no solvent), Time= 0.75h, T= 60 °C , Green chemistry, Solvent Hajipour, Abdol Reza; Karimi, Hirbod; Karimzadeh, Morteza; Monatshefte fur Chemie; vol. 145; nb. 9; (2014); p. 1461 1472 View in Reaxys

89 %

General experimental procedure General procedure: To a mixture of substrate (1.0 mmol) and acetic anhydride (1.0 mmol), 0.008 g PVPP.OTf (3.4 molpercent) was added. The mixture was stirred at room temperature for the time indicated in Tables 2, 3 and 4. The progress of the reaction was followed by TLC or GC for aliphatic alcohols. After completion of the reaction, ethyl acetate (2 9 10 cm3) was added, and the catalyst was separated by filtration. The filtrate was washed with an aqueous solution of NaHCO3 (10percent, 2 9 10 cm3) and water (2 9 10 cm3) and dried with Na2SO4. The solvent was evaporated under reduced pressure to afford the expected product.

With polyvinylpolypyrrolidone supported triflic acid in neat (no solvent), Time= 0.366667h, T= 20 °C , Green chemistry Tajbakhsh, Mahgol; Tajbakhsh, Mahmoud; Khaksar, Samad; Gazvini, Helia Janatian; Heidary, Marzieh; Monatshefte fur Chemie; vol. 148; nb. 6; (2017); p. 1117 - 1122 View in Reaxys

88 %

With Sulfate, tin(IV) oxide, Time= 0.5h, T= 20 °C Satam, Jitendra R.; Gawande, Manoj B.; Deshpande, Sameer S.; Jayaram, Radha V.; Synthetic Communications; vol. 37; nb. 17; (2007); p. 3011 - 3020 View in Reaxys

87 %

With pyridine in benzene, Time= 4h, Heating Yoh, Soo-Dong; Kang, Joong-Kyu; Kim, Sung-Hong; Tetrahedron; vol. 44; nb. 8; (1988); p. 2167 - 2174

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View in Reaxys 87 %

With silica sulfate in dichloromethane, Time= 0.025h, T= 20 °C Jin, Tong-Shou; Zhao, Ying; Liu, Li-Bin; Chen, Zhuo; Li, Tong-Shuang; Synthetic Communications; vol. 36; nb. 9; (2006); p. 1221 - 1227 View in Reaxys

86 %

in neat (no solvent), Time= 0.583333h, T= 20 °C , Green chemistry Farhadi, Saeed; Jahanara, Kosar; Sepahdar, Asma; Journal of the Iranian Chemical Society; vol. 11; nb. 4; (2014); p. 1103 1112 View in Reaxys

86 %

Catalytic tests General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 °C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10percent solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data. in neat (no solvent), Time= 0.633333h, T= 75 °C Farhadi, Saeed; Jahanara, Kosar; Chinese Journal of Catalysis; vol. 35; nb. 3; (2014); p. 368 - 375 View in Reaxys

86 %

With tetrabutylammomium bromide, potassium carbonate, Time= 0.166667h, T= 100 °C , p= 760.051Torr , Microwave irradiation Selvakumar, Kodirajan; Prasath Lingam, Kandapalam Arun; Luxmi Varma, Rama Varma; RSC Advances; vol. 4; nb. 69; (2014); p. 36538 - 36543 View in Reaxys

85 %

With bismuth oxide perchlorate, Time= 0.5h, T= 20 °C Chakraborti, Asit K.; Gulhane, Rajesh; Shivani; Synlett; nb. 12; (2003); p. 1805 - 1808 View in Reaxys

85 %

With beta zeolite H-form, Time= 2h, T= 20 °C Bhaskar, Pallooru Muni; Loganathan, Duraikkannu; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 43; nb. 4; (2004); p. 892 - 894 View in Reaxys

85 %

With polyvinylpolypyrrolidone-bound boron trifluoride in acetonitrile, Time= 2h, T= 20 °C Mokhtary, Masoud; Qandalee, Mohammad; Najafizadeh, Faranak; Comptes Rendus Chimie; vol. 15; nb. 5; (2012); p. 389 393 View in Reaxys

84 %

in neat (no solvent), T= 150 °C , Microwave irradiation Kim, Bo Ram; Sung, Gi Hyeon; Lee, Sang-Gyeong; Yoon, Yong Jin; Tetrahedron; vol. 69; nb. 15; (2013); p. 3234 - 3237 View in Reaxys

83 %

With Montmorillonite KSF, Time= 3.5h, Ambient temperature Li, Ai-Xiao; Li, Tong-Shuang; Ding, Tian-Hui; Chemical Communications; nb. 15; (1997); p. 1389 - 1390 View in Reaxys

83 %

With Montmorillonite KSF, Time= 3.5h, Ambient temperature Li, Tong-Shuang; Li, Ai-Xiao; Journal of the Chemical Society - Perkin Transactions 1; nb. 12; (1998); p. 1913 - 1917 View in Reaxys

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83 %

With bismuth(III) nitrate, silica gel, Time= 0.0333333h, microwave irradiation Asadolah, Karim; Heravi, Majid M.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 11; (2004); p.

2335 - 2339 View in Reaxys

83 %

With silica-supported zinc chloride in acetonitrile, Time= 3.5h, T= 80 °C Gupta, Raman; Kumar, Vineet; Gupta, Monika; Paul, Satya; Gupta, Rajive; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 47; nb. 11; (2008); p. 1739 - 1743 View in Reaxys

82 %

With montmorillonite acid clay, Time= 0.0833333h, microwave irradiation Mallavadhani, Uppuluri V.; Sahoo, Laxmidhar; Roy, Subhra; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 43; nb. 10; (2004); p. 2175 - 2177 View in Reaxys

81 %

With tantalum pentachloride in dichloromethane, Ambient temperature Chandrasekhar; Ramachander; Takhi, Mohamed; Tetrahedron Letters; vol. 39; nb. 20; (1998); p. 3263 - 3266 View in Reaxys

80 %

With acetic acid, triethylamine in dichloromethane, Time= 0.5h, Heating Lee, Chang Kiu; Yu, Ji Sook; Lee, Hye-Jin; Journal of Heterocyclic Chemistry; vol. 39; nb. 6; (2002); p. 1207 - 1217 View in Reaxys

80 %

Phenyl 3-Chlorobenzoate (1c); Typical Procedure General procedure: A 25 mL flask was charged with lithium (0.07 g, 9.68 mmol),naphthalene (0.19 g, 1.48 mmol), anhyd MnI2 (1.45 g, 4.71 mmol), and freshly distilled THF (10 mL) under argon pressure,and the mixture was stirred for 1 h at r.t. To the resultingslurry, containing 2.5 mmol of highly active manganese, wasadded PhOH (0.47 g, 5.0 mmol) and the resulting mixture wasstirred at r.t. for 10 min. Neat 3-chlorobenzoyl chloride (0.88 g,5.0 mmol) was then added to the flask, and the mixture wasstirred at r.t. for 30 min. The reaction was then quenched with3 M aq HCl, and the mixture was extracted with Et2O (3 × 10 mL).The organic layers were combined and washed with sat. aqNaHCO3 (3 × 10 mL), sat. aq Na2S2O3 (3 × 10 mL), and brine (3 ×10 mL), then dried (MgSO4). Column chromatography (silica gel,1percent EtOAc–hexanes) gave a pale-yellow solid.yield: 0.96 g (83percent).

Stage 1: With manganese(II) iodide, naphthalene, lithium in tetrahydrofuran, Time= 0.166667h, T= 20 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Time= 1h, T= 20 °C , Inert atmosphere Joo, Seong-Ryu; Youn, Young-Jin; Hwang, Young-Ran; Kim, Seung-Hoi; Synlett; vol. 28; nb. 19; (2017); p. 2665 - 2669 View in Reaxys

76 %

With silver hexafluoroantimonate, bis(benzonitrile)dichloroplatinum(II) in dichloromethane, Heating, Friedel-Crafts acylation Fuerstner, Alois; Voigtlaender, David; Schrader, Wolfgang; Giebel, Dirk; Reetz, Manfred T.; Organic Letters; vol. 3; nb. 3; (2001); p. 417 - 420 View in Reaxys

74 %

With 1H-imidazole, Time= 0.05h, Irradiation, microwave Hirose, Takuji; Kopek, Benjamin G.; Wang, Zhao-Hui; Yusa, Ritsuko; Baldwin, Bruce W.; Tetrahedron Letters; vol. 44; nb. 9; (2003); p. 1831 - 1833 View in Reaxys

70 %

Synthesis of substituted acetic acid phenyl ester General procedure: To a mixture of phenol a1 (94.1 g, 1 mol) and acetic anhydride (102 g, 1 mol) was added three drops of concentrated H2SO4 at room temperature with stirring for 10 min. TLC monitoring indicated that reaction was finished and acetic acid phenyl ester b1 was generated. The mixture was poured into water (500 mL) with stirring, extracted with EtOAc (10 × 50 mL) and the layers were separated. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Acetic acid phenyl ester b1 (95.3 g, 70percent) was obtained.

With sulfuric acid, Time= 0.166667h, T= 20 °C

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Tu, Qi-Dong; Li, Ding; Sun, Yao; Han, Xin-Ya; Yi, Fan; Sha, Yibamu; Ren, Yan-Liang; Ding, Ming-Wu; Feng, LingLing; Wan, Jian; Bioorganic and Medicinal Chemistry; vol. 21; nb. 11; (2013); p. 2826 - 2831 View in Reaxys 65 %

Typical Procedure General procedure: To a stirred solution of 2-naphthol (0.2 mmol) in TEAA(2 ml), was added acetic anhydride (0.22 mmol). The solutionwas stirred for 3 hours at room temperature. After consumptionof starting material (TLC monitoring, ethyl acetate/ hexane, 2:8), the product formed was diluted with 1 mlH2O and extracted with 3 x 2 ml ether. The combined organiclayer was separated, dried (Na2SO4), and evaporatedunder reduced pressure to afford the desired product. 1H and13C NMR spectra were in full accordance with the structureproposed. The water in the aqueous layer was distilled under reduced pressure leaving behind the TEAA which was furtherrecycled.

With triethylammonium acetate, Time= 4h, T= 20 °C Lafuente, Leticia; Díaz, Gisela; Bravo, Rodolfo; Ponzinibbio, Agustín; Letters in Organic Chemistry; vol. 13; nb. 3; (2016); p. 195 - 200 View in Reaxys

65 %

6.6 Acetylation of alcohols catalyzed by 1 General procedure: In a typical reaction, a 50-mL Schlenk flask was charged with 5.2 g (0.048 mol) of benzylalcohol in 10 mL of acetic anhydride and 0.02 molpercent of catalyst 1. The reaction mixture was stirred for 2 d at room temperature. The progress of the reaction was periodically monitored by NMR spectroscopy. The reaction was quenched with 10 mL with water. The organic layer was washed with 5percent NaHCO3 solution, dried over MgSO4 and distilled at 200–206 °C to yield 5.8 g (82percent) of benzyl acetate.

With [MeS(CH2)3]2SnCl2, Time= 72h, T= 20 °C , Schlenk technique Vargas, Diana Gabriela; Metta-Magaña, Alejandro; Sharma, Hemant K.; Whalen, Margaret M.; Gilbert, Thomas M.; Pannell, Keith H.; Inorganica Chimica Acta; vol. 468; (2017); p. 125 - 130 View in Reaxys

63 %

With tetradecafluorohexane, Time= 24h, T= 20 °C Peng, Zhihong; Orita, Akihiro; An, Delie; Otera, Junzo; Tetrahedron Letters; vol. 46; nb. 18; (2005); p. 3187 - 3189 View in Reaxys

55 %

in neat (no solvent), Time= 1h, T= 150 °C Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Kim, Jeum-Jong; Yoon, Yong-Jin; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3410 - 3414 View in Reaxys

40 %

With zinc(II) chloride, Time= 2.5h, T= 30 °C , Neat (no solvent) Yadav, Prakrati; Lagarkha, Rekha; Balla, Zahoor Ahmad; Asian Journal of Chemistry; vol. 22; nb. 7; (2010); p. 5155 5158 View in Reaxys

15 %

Stage 1: With aluminum (III) chloride in tetrahydrofuran, Time= 1h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 1h, Reflux Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Yoon, Hyo Jae; Lee, Sang-Gyeong; Yoon, Yong-Jin; Synlett; vol. 25; nb. 13; (2014); p. 1909 - 1915; Art.No: ST-2014-U0361-L View in Reaxys With perchloric acid, acetic acid Kuhn; Daxner; Monatshefte fuer Chemie; vol. 83; (1952); p. 689,693 View in Reaxys With camphor-10-sulfonic acid Reychler; Chem. Zentralbl.; vol. 79; nb. I; (1908); p. 1042 View in Reaxys Abdestillieren der entstehenden Essigsaeure

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Patent; Glidden Co.; US2212509; (1935) View in Reaxys Henriques; ; vol. 9; (1896); p. 224 View in Reaxys 90 % Chromat.

With LaNaY, T= 350 °C Rao, Y. V. Subba; Kulkarni, S. J.; Subrahmanyam, M.; Rao, A. V. Rama; Journal of the Chemical Society, Chemical Communications; nb. 18; (1993); p. 1456 - 1457 View in Reaxys With sulfuric acid Zenkevich; Kosman; Russian Journal of Physical Chemistry A; vol. 71; nb. 7; (1997); p. 1173 - 1176 View in Reaxys in 1,4-dioxane, water, T= 25 °C , Anion, pH 9.00, Rate constant Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys With perchloric acid, T= 5 °C , Acetylation Borisov; Sharafutdinova; Gusmanov; Mikhailov; Russian Journal of Physical Chemistry A; vol. 73; nb. 8; (1999); p. 1360 1362 View in Reaxys

98 % Chromat.

With K5CoIIIW12O40, Time= 0.0166667h, T= 20 °C Habibi; Tangestaninejad; Mirkhani; Yadollahi; Synthetic Communications; vol. 32; nb. 6; (2002); p. 863 - 867 View in Reaxys Neuvonen, Helmi; Neuvonen, Kari; Koch, Andreas; Kleinpeter, Erich; Pasanen, Paavo; Journal of Organic Chemistry; vol.

67; nb. 20; (2002); p. 6995 - 7003 View in Reaxys

97 % Chromat.

in water, Time= 0.00275h, T= 250 °C , p= 37503.8Torr Sato, Masahiro; Matsushima, Keiichiro; Kawanami, Hajime; Ikuhsima, Yutaka; Angewandte Chemie - International Edition; vol. 46; nb. 33; (2007); p. 6284 - 6288 View in Reaxys

94 % Chromat.

With chloromethyl polystyrene supported gadolinium triflate in dimethyl sulfoxide, Time= 0.0833333h, T= 20 °C Yoon, Hyo-Jin; Lee, Sang-Myung; Kim, Jong-Ho; Cho, Hong-Jun; Choi, Jung-Woo; Lee, Sang-Hyeup; Lee, Yoon-Sik; Tetrahedron Letters; vol. 49; nb. 19; (2008); p. 3165 - 3171 View in Reaxys With antimony(III) chloride, Time= 0.416667h, T= 20 °C Bhattacharya, Asish K.; Diallo, Mamadou A.; Ganesh, Krishna N.; Synthetic Communications; vol. 38; nb. 10; (2008); p.

1518 - 1526 View in Reaxys

97 %Chromat.

With 1-butyl-3-methylimidazolium 4-methylbenzenenesulfonate, 1-butyl-3-methylimidazolium Tetrafluoroborate, Time= 0.166667h, T= 50 °C Liu, Ye; Liu, Lu; Lu, Yong; Cai, Yue-Qin; Monatshefte fur Chemie; vol. 139; nb. 6; (2008); p. 633 - 638 View in Reaxys With sulfuric acid Li, Yong; Yang, Zhengyin; Journal of Coordination Chemistry; vol. 63; nb. 11; (2010); p. 1960 - 1968 View in Reaxys Li, Yong; Yang, Zheng-Yin; Wu, Jin-Cai; European Journal of Medicinal Chemistry; vol. 45; nb. 12; (2010); p. 5692 - 5701

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View in Reaxys 93 %Chromat.

With bismuth (III) nitrate pentahydrate, Time= 2.3h, T= 25 °C Heravi; Behbahani; Daroogheha; Oskooie; Russian Journal of Organic Chemistry; vol. 45; nb. 7; (2009); p. 1108 - 1109 View in Reaxys With sulfuric acid Li, Yong; Yang, Zheng-Yin; Liao, Zhen-Chuan; Han, Zi-Chao; Liu, Zeng-Chen; Inorganic Chemistry Communications; vol. 13; nb. 10; (2010); p. 1213 - 1216 View in Reaxys

100 %Chro- With [Ti(IV)(salophen)(OTf)2] in dichloromethane, Time= 0.0166667h, T= 20 °C mat.

Yadegari, Maryam; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Mohammadpoor-Baltork, Iraj; Polyhedron; vol. 30; nb. 13; (2011); p. 2237 - 2243 View in Reaxys 94 %Chromat.

With iron(III) phosphate, Time= 12h, T= 20 °C , chemoselective reaction Behbahani; Farahani; Oskooie; Journal of the Korean Chemical Society; vol. 55; nb. 4; (2011); p. 633 - 637 View in Reaxys With sulfuric acid Li, Yong; Yang, Zheng-Yin; Journal of Fluorescence; vol. 20; nb. 1; (2010); p. 329 - 342 View in Reaxys Li, Yong; Yang, Zheng-Yin; Li, Tian-Rong; Liu, Zeng-Chen; Wang, Bao-Dui; Journal of Fluorescence; vol. 21; nb. 3; (2011); p. 1091 - 1102 View in Reaxys

97 %Chromat.

With 5,10,15,20-tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate in acetonitrile, Time= 0.05h, T= 20 °C Taghavi, S. Abdolmanaf; Moghadam, Majid; Mohammadpoor-Baltork, Iraj; Tangestaninejad, Shahram; Mirkhani, Valiollah; Khosropour, Ahmad Reza; Inorganica Chimica Acta; vol. 377; nb. 1; (2011); p. 159 - 164 View in Reaxys basic conditions Sharma, Vinay Prabha; Kumar, Praveen; Sharma, Meenakshi; Asian Journal of Chemistry; vol. 23; nb. 10; (2011); p. 4616 - 4620 View in Reaxys With sodium hydroxide Joshi, Vidya; Govind Hatim, Jaywant; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 51; nb.

7; (2012); p. 1002 - 1010 View in Reaxys

100 %Chro- With [tetrabutylammonium]8 5,10,15,20-tetrakis(4-hexamolybdato)-porphyrinatotin(IV) chloride in acetonitrile, Time= 0.1h, mat.

T= 20 °C Araghi, Mehdi; Mirkhani, Valiollah; Moghadam, Majid; Tangestaninejad, Shahram; Mohammdpoor-Baltork, Iraj; Dalton Transactions; vol. 41; nb. 38; (2012); p. 11745 - 11752 View in Reaxys With C13H16NO6S2 (1+)*HO4S(1-), Time= 0.1h, T= 25 °C , Green chemistry Zhu, Lili; Liang, Xuezheng; Kinetics and Catalysis; vol. 53; nb. 6; (2012); p. 684 - 688; Kinet. Katal.; vol. 53; nb. 6; (2012); p.

728 - 732 View in Reaxys 99 %Chromat.

With sulfonated ordered mesoporous carbon (CMK-5-SO3H) in neat (no solvent), Time= 0.166667h, T= 20 °C , Green chemistry

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Zareyee, Daryoush; Alizadeh, Parastoo; Ghandali, Mohammad S.; Khalilzadeh, Mohammad A.; Chemical Papers; vol. 67; nb. 7; (2013); p. 713 - 721 View in Reaxys With sulfuric acid Liu, Zeng-Chen; Yang, Zheng-Yin; Li, Yan-Xia; Wang, Bao-Dui; Li, Yong; Li, Tian-Rong; Ding, Yong-Jie; Journal of Fluorescence; vol. 23; nb. 6; (2013); p. 1239 - 1245 View in Reaxys With sulfuric acid, T= 20 °C Zhu, Wufu; Chen, Chen; Sun, Chengyu; Xu, Shan; Wu, Chunjiang; Lei, Fei; Xia, Hui; Tu, Qidong; Zheng, Pengwu; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 64 - 73 View in Reaxys 92 %Chromat.

2.4. General procedure for acylation reaction General procedure: A 25mL sealed tube containing a magnetic stir bar was charged with phenol/alcohol/amine (1mmol) and acetic anhydride (1.5mmol), nano γ-Fe2O3 (5molpercent, 8mg) as catalyst. The reaction mixture was kept for sonication in sonication bath at room temperature (28°C) for 1h. The ultrasonic bath (Labman Scientific Instruments, Model – LMUC 4) had a frequency of 33kHz and electric power rating of 100W. The reaction progress was monitored on thin-layer chromatography (TLC) and gas chromatography (PerkinElmer, GC Clarus 400) analysis. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and catalyst was separated from reaction mixture by using a strong magnet. The separated catalyst was washed with distilled water and absolute ethanol several times then dried in oven and reused for further reaction. The reaction mixture was washed with saturated NaHCO3 solution (1×15mL) and the product was extracted with ethyl acetate (3×10mL) and dried over Na2SO4 and evaporated under vacuum. All the obtained products are well known in the literature and were confirmed by gas chromatography–mass spectrometry (Shimadzu GCMS-QP 2010) analysis by comparison with literature data.

With Magnetically separable γ-Fe2O3 nanoparticles in neat (no solvent), Time= 1h, T= 28 °C , Sealed tube, Sonication, Catalytic behavior, Reagent/catalyst, Time Bhosale, Manohar A.; Ummineni, Divya; Sasaki, Takehiko; Nishio-Hamane, Daisuke; Bhanage, Bhalchandra M.; Journal of Molecular Catalysis A: Chemical; vol. 404-405; (2015); p. 8 - 17 View in Reaxys With pyridine, T= 0 - 20 °C Gadakh, Sunita K.; Dey, Soumen; Sudalai, Arumugam; Journal of Organic Chemistry; vol. 80; nb. 22; (2015); p. 11544 11550 View in Reaxys a With sulfuric acid Dalal, Aarti; Khanna, Radhika; Berar, Urmila; Kamboj, Ramesh C.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 329; (2016); p. 238 - 245 View in Reaxys 1 : Example 1 is the preparation of phenol acetate 21.4 g (i.e., 0.21 mol) of acetic anhydride and 18.8 g (i.e., 0.2 mL) of phenol were well mixed and placed in an ice-water bath,Adding 3 drops of concentrated sulfuric acid to the inside, shaking, fractionating acetic acid, and collecting 194 to 196 ° C fractions to obtain colorless and transparent liquid phenol acetate, and can reach 90percent recovery rate. , Cooling with ice Patent; Chen, Yumei; (5 pag.); CN105585545; (2016); (A) Chinese View in Reaxys With pyridine, T= 100 °C Dofe, Vidya S.; Sarkate, Aniket P.; Kathwate, Santosh H.; Gill, Charansingh H.; Heterocyclic Communications; vol. 23; nb.

4; (2017); p. 325 - 330 View in Reaxys

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Dofe, Vidya S.; Sarkate, Aniket P.; Shaikh, Zarina M.; Gill, Charansingh H.; Heterocyclic Communications; vol. 24; nb. 1; (2018); p. 59 - 65 View in Reaxys

O

O

O

O

O

OH

Rx-ID: 33753243 View in Reaxys 2/238 Yield

Conditions & References

31 %

With dipotassium peroxodisulfate, silver(I) acetate in acetonitrile, Time= 24h, T= 100 °C Seo, Sangwon; Taylor, John B.; Greaney, Michael F.; Chemical Communications; vol. 48; nb. 66; (2012); p. 8270 - 8272 View in Reaxys Reaction Steps: 3 1: acetonitrile / 2 h / 20 °C / Darkness 2: acetonitrile / Darkness 3: water / d7-N,N-dimethylformamide / 2.5 h / 100 °C / Inert atmosphere; Glovebox; Sealed tube; Darkness With water in d7-N,N-dimethylformamide, acetonitrile Crovak, Robert A.; Hoover, Jessica M.; Journal of the American Chemical Society; vol. 140; nb. 7; (2018); p. 2434 - 2437 View in Reaxys

O O O

O

O

(v4)

N

Ag+

O–

(v3)

(v2)

N (v4)

Rx-ID: 47488264 View in Reaxys 3/238 Yield

Conditions & References With water in d7-N,N-dimethylformamide, Time= 2.5h, T= 100 °C , Inert atmosphere, Glovebox, Sealed tube, Darkness, Kinetics, Time Crovak, Robert A.; Hoover, Jessica M.; Journal of the American Chemical Society; vol. 140; nb. 7; (2018); p. 2434 - 2437 View in Reaxys

O

O

O

O Ag+ O–

O

Rx-ID: 47488329 View in Reaxys 4/238 Yield

Conditions & References Reaction Steps: 2 1: acetonitrile / Darkness 2: water / d7-N,N-dimethylformamide / 2.5 h / 100 °C / Inert atmosphere; Glovebox; Sealed tube; Darkness With water in d7-N,N-dimethylformamide, acetonitrile Crovak, Robert A.; Hoover, Jessica M.; Journal of the American Chemical Society; vol. 140; nb. 7; (2018); p. 2434 - 2437

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View in Reaxys

O

O

OH

O

HO

Rx-ID: 643075 View in Reaxys 5/238 Yield 98 %

Conditions & References With bismuth(lll) trifluoromethanesulfonate, Time= 1h, Heating Mohammadpoor-Baltork; Khosropour; Aliyan; Journal of Chemical Research - Part S; nb. 7; (2001); p. 280 - 282 View in Reaxys

97 %

With tetrachloromethane, triethylamine, triphenylphosphine in acetonitrile, Time= 4h, Ambient temperature Hashimoto, Shizunobu; Furukawa, Isao; Bulletin of the Chemical Society of Japan; vol. 54; nb. 7; (1981); p. 2227 - 2228 View in Reaxys

96.5 %

With ZSM-35 zeolite in acetonitrile, Time= 8h, Heating Srivastava; Venkatathri; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 43; nb. 4; (2004); p.

888 - 891 View in Reaxys

96 %

With 50wtpercent Cs2.5H0.5PW12O40 supported on MCM-41 in acetonitrile, Time= 0.5h, T= 50 °C Rana, Surjyakanta; Mallick, Sujata; Rath, Dharitri; Parida; Journal of Chemical Sciences; vol. 124; nb. 5; (2012); p. 1117 1125 View in Reaxys

93 %

2.5 Typical procedure of acetylation General procedure: The substrate (alcohol, phenol or amine; 1.0 mmol) was treated with Ac2O (2.0 mmol) in the presence of P(4-VPH)ClO4 (50 mg) at room temperature under solvent-free conditions and magnetic stirring. After completion of the reaction as indicated by TLC, the mixture was diluted with Et2O (25 ml) and the catalyst allowed to settle down. The supernatant ethereal solution was decanted off, the catalyst washed with Et2O (2 ml) and the combined ethereal solution concentrated under vacuum to afford the product, identical(mp, IR, 1H and 13C NMR, and GC–MS) to an authentic sample of acetylated product.

The recovered catalyst was dried at 50 °C under vacuum for 2 h. The recovered catalyst, after drying, was reused for four more consecutive acetylation reactions of benzyl alcohol (1.0 mmol) affording 96, 96, 94, and 94percent yields, respectively, in 22, 23, 23, and 25 min (Scheme 2).

With poly(4-vinylpyridine) perchlorate in neat (no solvent), Time= 0.333333h, T= 20 °C Khaligh, Nader Ghaffari; Journal of Molecular Catalysis A: Chemical; vol. 363-364; (2012); p. 90 - 100 View in Reaxys

92 %

With triphenylphosphine, diethylazodicarboxylate in tetrahydrofuran, Ambient temperature Grochowski, Edward; Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques; vol. 28; nb. 7-8; (1980); p. 489 - 497 View in Reaxys

92 %

With triphenylphosphine, diethylazodicarboxylate in tetrahydrofuran, Ambient temperature, other phenols and carboxylic acids, Mechanism Grochowski, Edward; Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques; vol. 28; nb. 7-8; (1980); p. 489 - 497 View in Reaxys

90 %

9 :Toluene (100 ml), phenol (8.94 g, 95 mmol) and acetic acid (6.05 g, 100 mmol) were added into a 200-ml flask in this order at room temperature and then p-toluenesulfonic acid monohydrate (2.85 g, 15 mmol) was charged thereto. The solution was gently heated and subjected to reflux dehydration for 3 to 5 hours. After reflux dehydration, the solution was cooled to around room temperature, added with triethylamine (2.40 g, 25 mmol) at room temperature, stirred and then added with silica gel. After continuing to stir for a while, the silica gel was filtered off. After the solvent of the filtrate was removed in vacuum distillation, phenyl acetate (11.64 g, 90percent) was isolated in distillation.

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With toluene-4-sulfonic acid in toluene, Time= 5h, T= 20 °C , Reflux Patent; WAKO PURE CHEMICAL INDUSTRIES, LTD.; US2010/324314; (2010); (A1) English View in Reaxys 88 %

With cetyltrimethylammonium chloride, potassium hexacyanoferrate(III), Time= 2h, T= 80 °C Dewan, Anindita; Bora, Utpal; Kakati, Dilip Kumar; Bulletin of the Korean Chemical Society; vol. 31; nb. 12; (2010); p.

3870 - 3871 View in Reaxys

68 %

With diethyl(trichloromethyl)phosphine, triethylamine in dichloromethane, Time= 12h, Ambient temperature Majewski, Piotr; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 55; nb. 1-4; (1991); p. 185 - 194 View in Reaxys

68 %

With pyridine, N-Bromosuccinimide, triphenylphosphine in dichloromethane, Time= 2h, Ambient temperature Froeyen, Paul; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 91; nb. 1-4; (1994); p. 145 - 152 View in Reaxys

68 %

With phosphorus pentoxide, silica gel, Time= 6h, T= 25 °C Eshghi; Rafei; Karimi; Synthetic Communications; vol. 31; nb. 5; (2001); p. 771 - 774 View in Reaxys

65 %

With carbon-silica composite from starch (7.5 molpercent SO3H), Time= 6h, T= 60 °C , solvent-free conditions Gupta, Princy; Paul, Satya; Green Chemistry; vol. 13; nb. 9; (2011); p. 2365 - 2372 View in Reaxys

20 %

Catalytic test General procedure: testIn all the reactions, a 25 cm3round-bottomed flask, at thereaction temperature and connected with a water jacketed con-denser, was used. In a typical experience, the reactor was loadedwith a mixture of 1 mmol of 2-phenylethanol (122 mg), 5 mmolof acetic acid (300 mg), 5 cm3of toluene and 100 mg of the cata-lyst. The mixture was stirred at 700 rpm.

Samples were withdrawnfrom the organic phase at different intervals (1, 3, 5, 7, 10 and14 h). Each sample volume was approximately 10 mm3and wasdiluted with 2 cm3of acetonitrile. The concentration of substrateswas calculated with the corresponding areas, using a ShimadzuHP2010 gas chromatography instrument (Chromopack CP Sil 8 CB,30 m × 0.32 mm ID). A similar procedure was followed with theother studied alcohols and phenols.After 14 h of reaction, the solution was concentrated undervacuum, and the residue was purified by column chromatogra-phy employing silica gel as the stationary phase and a mixtureof hexane-ethyl acetate as the elution solvent. The reaction prod-ucts were identified by chromatographic comparison with standardsamples. The conversion was expressed as the ratio of moles ofproducts to moles of initial alcohol.

With tungstophosphoric acid-modified zirconia in toluene, Time= 14h, T= 110 °C Osiglio, Lilian; Sathicq, Gabriel; Pizzio, Luis; Romanelli, Gustavo; Blanco, Mirta; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 88 - 96 View in Reaxys

16 %

Time= 24h, T= 117 °C , Esterification Brown, James S.; Glaeser, Roger; Liotta, Charles L.; Eckert, Charles A.; Chemical Communications; nb. 14; (2000); p.

1295 - 1296 View in Reaxys

15 %

With S4B15W12.5 borated zirconia modified with ammonium metatungstate in toluene, Time= 14h, T= 110 °C Osiglio, Lilian; Sathicq, Angel G.; Romanelli, Gustavo P.; Blanco, Mirta N.; Journal of Molecular Catalysis A: Chemical; vol. 359; (2012); p. 97 - 103 View in Reaxys

10 %

With borated zirconia in toluene, Time= 14h, T= 110 °C Osiglio, Lilian; Romanelli, Gustavo; Blanco, Mirta; Journal of Molecular Catalysis A: Chemical; vol. 316; nb. 1-2; (2010); p.

52 - 58 View in Reaxys

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10 %

With zirconocene bis(perfluorooctanesulfonate) trihydrate*(tetrahydrofuran) in neat (no solvent), T= 80 °C , Sealed tube, Green chemistry, chemoselective reaction Tang, Zhi; Jiang, Qiutao; Peng, Lifen; Xu, Xinhua; Li, Jie; Qiu, Renhua; Au, Chak-Tong; Green Chemistry; vol. 19; nb.

22; (2017); p. 5396 - 5402 View in Reaxys

9%

With acid activated Indian bentonite in toluene, Time= 8h, Heating Vijayakumar; Iyengar, Pushpa; Nagendrappa, Gopalpur; Prakash, B. S. Jai; Journal of the Indian Chemical Society; vol.

82; nb. 10; (2005); p. 922 - 925 View in Reaxys With PPA Nakazawa; Matsuura; Yakugaku Zasshi; vol. 74; (1954); p. 69; ; (1955); p. 1631 View in Reaxys With trichlorophosphate Nencki; Journal fuer Praktische Chemie (Leipzig); vol. <2> 25; (1882); p. 277 View in Reaxys With sodium tetrahydroborate, 2) reflux, 12 h, Yield given. Multistep reaction Prashad, Mahavir; Jigajinni, Veerappa B.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 19; nb. 9; (1980); p. 822 - 823 View in Reaxys With Yb(p-toluenesulfonate)3, Time= 18h, Heating Parac-Vogt, Tatjana N.; Deleersnyder, Karen; Binnemans, Koen; European Journal of Organic Chemistry; nb. 9; (2005); p.

1810 - 1815 View in Reaxys With Starbon(R) 400-SO3H, Time= 0.166667h, T= 130 °C , microwave irradiation Budarin, Vitaly L.; Clark, James H.; Luque, Rafael; Macquarrie, Duncan J.; Chemical Communications; nb. 6; (2007); p.

634 - 636 View in Reaxys With H5PMo10V2O40, Time= 0.166667h, Microwave irradiation, neat (no solvent) Tayebee, Reza; Zonoz, Farokhzad Mohammadi; Journal of the Korean Chemical Society; vol. 55; nb. 3; (2011); p. 541 - 545 View in Reaxys With dmap in dichloromethane, Time= 20h, T= 20 °C Keese, Reinhart; Berdat, Francois; MacChi, Piero; Journal of Organic Chemistry; vol. 78; nb. 5; (2013); p. 1965 - 1970 View in Reaxys

O

O

O

Rx-ID: 716484 View in Reaxys 6/238 Yield 99 %

Conditions & References With oxone, silica gel in dichloromethane, Time= 16h, T= 20 °C , Baeyer-Villiger oxidation Gonzalez-Nunez, Maria E.; Mello, Rossella; Olmos, Andrea; Asensio, Gregorio; Journal of Organic Chemistry; vol. 70; nb.

26; (2005); p. 10879 - 10882 View in Reaxys

89 %

With 3-chloro-benzenecarboperoxoic acid in water, Time= 2h, T= 80 °C , Oxidation

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Raap, Jan; Nieuwenhuis, Saskia; Creemers, Alain; Hexspoor, Sander; Kragl, Udo; Lugtenburg, Johan; European Journal of Organic Chemistry; nb. 10; (1999); p. 2609 - 2621 View in Reaxys 85 %

With 3-chloro-benzenecarboperoxoic acid in water, Time= 1.5h, T= 80 °C Fringuelli, Francesco; Germani, Raimondo; Pizzo, Ferdinandino; Savelli, Gianfranco; Gazzetta Chimica Italiana; vol. 119; nb. 4; (1989); p. 249 - 250 View in Reaxys

85 %

With 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in dichloromethane, Time= 48h, Ambient temperature Kotsuki, Hiyoshizo; Arimura, Koji; Araki, Tomohiro; Shinohara, Toshio; Synlett; nb. 4; (1999); p. 462 - 464 View in Reaxys

85 %

With 3-chloro-benzenecarboperoxoic acid, 1-butyl-3-methylimidazolium Tetrafluoroborate, Time= 5h, T= 27 °C , Baeyer-Villiger oxidation Yadav; Reddy; Basak; Narsaiah; Chemistry Letters; vol. 33; nb. 3; (2004); p. 248 - 249 View in Reaxys

80 %

With sodium perborate in acetic acid, trifluoroacetic acid, Time= 8h, Ambient temperature McKillop, Alexander; Tarbin, Jonathan A.; Tetrahedron; vol. 43; nb. 8; (1987); p. 1753 - 1758 View in Reaxys

80 %

With dihydrogen peroxide, iodine, acetic acid, Time= 1h, T= 20 °C , Baeyer-Villiger oxidation Gaikwad, Digambar D.; Dake, Satish A.; Kulkarni, Ravibhushan S.; Jadhav, Wamanrao N.; Kakde, Shankar B.; Pawar, Rajendra P.; Synthetic Communications; vol. 37; nb. 23; (2007); p. 4093 - 4097 View in Reaxys

79 %

With oxygen, benzaldehyde, nickel(II) iodide, Dowex 50W, iron(II) in 1,2-dichloro-ethane, Time= 8h, T= 20 °C , Baeyer-Villiger oxidation Hashemi; Beni; Journal of Chemical Research - Part S; nb. 4; (2000); p. 196 - 197 View in Reaxys

75 %

With 3-chloro-benzenecarboperoxoic acid, trifluoroacetic acid in dichloromethane, Time= 8h, 0 deg C to room temperature Koch, Stacie S. Canan; Chamberlin, A. Richard; Synthetic Communications; vol. 19; nb. 5and6; (1989); p. 829 - 834 View in Reaxys

70 %

With hydrogenchloride, 4-amino-2-chloroperbenzoic acid in dichloromethane, Time= 5h, T= 20 °C , Baeyer-Villiger oxidation Hashemi, Mohammed M.; Ghazanfari, Dadkhoda; Ahmadibeni, Yousef; Karimi-Jaberi, Zahed; Ezabadi, Ali; Synthetic Communications; vol. 35; nb. 8; (2005); p. 1103 - 1107 View in Reaxys

67 %

2.3.1. Under MW irradiation General procedure: A mixture of m-CPBA (0.66 g, 3.9 mmol) and 5γ-pregnan-3,17-dione (1.5 mmol) in CHCl3 (10 ml) were irradiated in a closed vessel in a Synthon 3000 microwave reactor at 350 W, 105 °C and 7.1 bar for 5 min. The reaction mixture was then allowed to cool to room temperature and washed subsequently with 10percent Na2SO3 (2 x 100 ml) and aq. 10percent NaHCO3 (2 x 100 ml). The organic phase was dried over anhydrous Na2SO4 and evaporated under reduced pressure which was further purified by column chromatography over silica gel using 1:10 ethyl acetate-hexane as the eluent to furnish the pure lactones 17γ-acetoxy-3-oxa-A-homo-5γ-androstan-4-one (1a) and 17γ-acetoxy-4-oxa-A-homo-5γ-androstan-3-one (1b).

With 3-chloro-benzenecarboperoxoic acid in chloroform, Time= 0.05h, T= 105 °C , p= 5325.53Torr , Microwave irradiation, Baeyer-Villiger oxidation Borah, Juri Moni; Chowdhury, Pritish; Steroids; vol. 76; nb. 12; (2011); p. 1341 - 1345 View in Reaxys

42 %

2.3. General Procedures of BV oxidation General procedure: Ionic hybrid (0.5 mmol) and ketone (10 mmol) was added toa 25mL flask equipped with a condenser and magnetic stirrer. The reaction was started after the addition of H2O2 aqueous (35 wt.percent, 25mmol)in dropwise at 50 °C un-

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der vigorous stirring. The progress of the reaction was monitored by TLC (hexane/ethyl acetate=4/1). After the completion,the mixture was extracted with diethyl ether (3 × 15 mL).The combined organic layer was washed with aqueous of NaHCO3(3 × 15 mL) and water (3 × 15 mL), then dried over anhydrous MgSO4, filtered, and concentrated under vacuum to afford the crude product. The crude product was purified by column chromatography using hexane–ethyl acetate 4:1 (V/V) as eluent. The obtained product was identified by comparing TLC, 1H NMR and IR spectra data with authentic sample. The catalyst was recovered by washed with diethylether (3 × 10 mL), and then dried under vacuum at 80 °C over 8 h.Oxidant efficiency is determined by iodometric titration methods described in literature [25]. The results revealed that the amount of H2O2 present at the reaction endpoint was 2–3 mmol.

With dihydrogen peroxide in water, Time= 3h, T= 50 °C , Baeyer-Villiger Ketone Oxidation, Catalytic behavior, Reagent/catalyst Li, Xinzhong; Cao, Rong; Lin, Qi; Catalysis Communications; vol. 63; (2015); p. 79 - 83 View in Reaxys 3%

With 3-chloro-benzenecarboperoxoic acid in acetonitrile, Time= 0.75h, T= 80 °C , Baeyer-Villiger Ketone Oxidation, regioselective reaction Gambarotti, Cristian; Bjørsvik, Hans-René; Journal of Physical Organic Chemistry; vol. 28; nb. 10; (2015); p. 619 - 628 View in Reaxys With o-nitroperoxybenzoic acid, ortho-nitrobenzoic acid in chloroform, T= 30 °C , Rate constant, Mechanism Token, Katsuo; Hirano, Kenji; Yokoyama, Tai; Goto, Katsumi; Bulletin of the Chemical Society of Japan; vol. 64; nb. 9; (1991); p. 2766 - 2771 View in Reaxys With peracetic acid, toluene-4-sulfonic acid, acetic acid Ballio; Almirante; Annali di Chimica (Rome, Italy); vol. 41; (1951); p. 421,423 View in Reaxys With disodium hydrogenphosphate, dichloromethane, trifluoroacetyl peroxide Hawthorne et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 6393,6394, 6396 View in Reaxys

85 % Chromat.

With dihydrogen peroxide in dichloromethane, 1) 4 h, room temperature; 2) reflux, 8 h Pande, C. S.; Jain, N.; Synthetic Communications; vol. 19; nb. 7,8; (1989); p. 1271 - 1280 View in Reaxys With maleic anhydride, urea-hydrogen peroxide complex in dichloromethane, Time= 48h, Ambient temperature, Yield given Astudillo, Luis; Galindo, Antonio; Gonzalez, Antonio G.; Mansilla, Horacio; Heterocycles; vol. 36; nb. 5; (1993); p. 1075 1080 View in Reaxys

20 % Turnov.

With 1,1,1,3',3',3'-hexafluoro-propanol, 3-chloro-benzenecarboperoxoic acid in phosphate buffer, dichloromethane, Time= 3h, T= 20 °C , pH= 7.6, Baeyer-Villiger oxidation Kobayashi, Satoru; Tanaka, Hiroaki; Amii, Hideki; Uneyama, Kenji; Tetrahedron; vol. 59; nb. 9; (2003); p. 1547 - 1552 View in Reaxys With Sn-palygorskite, dihydrogen peroxide in 1,4-dioxane, Time= 24h, T= 70 °C , Baeyer-Villiger oxidation Lei, Ziqiang; Zhang, Qinghua; Luo, Jujie; He, Xiaoyan; Tetrahedron Letters; vol. 46; nb. 20; (2005); p. 3505 - 3508 View in Reaxys

66 % Chromat.

With 3-chloro-benzenecarboperoxoic acid, ammonium cerium(IV) nitrate in dichloromethane, T= 20 °C , Baeyer-Villiger oxidation Goswami, Papori; Hazarika, Saroj; Das, Archana M.; Chowdhury, Pritish; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 43; nb. 6; (2004); p. 1275 - 1281 View in Reaxys

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38 % Chromat.

With boron trifluoride diethyl etherate, water, 3-chloro-benzenecarboperoxoic acid, acetic acid, Time= 24h, T= 25 - 30 °C , Baeyer-Villiger oxidation Ochiai, Masahito; Takeuchi, Yasunori; Katayama, Tomoko; Sueda, Takuya; Miyamoto, Kazunori; Journal of the American Chemical Society; vol. 127; nb. 35; (2005); p. 12244 - 12245 View in Reaxys With oxone, potassium peroxomonosulfate, silica gel in carbon dioxide, T= 40 °C , p= 187515Torr , Baeyer-Villiger oxidation Gonzalez-Nunez, Maria E.; Mello, Rossella; Olmos, Andrea; Asensio, Gregorio; Journal of Organic Chemistry; vol. 71; nb.

17; (2006); p. 6432 - 6436 View in Reaxys With dihydrogen peroxide, tin, magnesium silicate aluminate in 1,4-dioxane, Time= 24h, T= 70 °C , Bayer-Villiger oxidation Lei, Ziqiang; Zhang, Qinghua; Wang, Rongmin; Ma, Guofu; Jia, Chengguo; Journal of Organometallic Chemistry; vol.

691; nb. 26; (2006); p. 5779 - 5785 View in Reaxys With dihydrogen peroxide, γ-Keggin-type silicodecatungstate dimer in nitromethane, water, Time= 2.25h, T= 59.85 °C , BaeyerVilliger oxidation Yoshida, Akihiro; Yoshimura, Masayuki; Uehara, Kazuhiro; Hikichi, Shiro; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 45; nb. 12; (2006); p. 1956 - 1960 View in Reaxys With [SiO2]-CH2CH2CO3H in supercritical carbon dioxide, T= 40 °C , p= 187519Torr , Flow conditions, Baeyer-Villiger oxidation Mello, Rossella; Olmos, Andrea; Parra-Carbonell, Javier; Gonzalez-Nunez, Maria Elena; Asensio, Gregorio; Green Chemistry; vol. 11; nb. 7; (2009); p. 994 - 999 View in Reaxys

30 %Chromat.

With Oxone, Time= 12h, T= 40 °C , Ionic liquid, Baeyer-Villiger oxidation Chrobok, Anna; Tetrahedron; vol. 66; nb. 32; (2010); p. 6212 - 6216 View in Reaxys 2.3 Biotransformations General procedure: Whole-cell biotransformations were performed in 40mL amber glass vials using 1mL reaction volumes. The biotransformation reaction mixture (BRM) consisted of 0.1g wet weight/mL in 200mM Tris-HCl (pH 8), 100mM glucose and 100mM glycerol. The reactions were initiated by the addition of substrate (10mM) dissolved in methanol. Reactions were performed at 20°C for 2h, where after the reactions were stopped and extracted using an equal volume (2 times 0.5mL) of ethyl acetate containing 2mM 1-undecanol or 2mM 3-octanol as internal standard. GC-MS analysis was carried out on a Finnigan Trace GC ultra (ThermoScientific) equipped with a FactorFour VF-5ms column (60m×0.32mm×0.25μm, Varian). Chiral separation (Table S2) was performed using either a Chiraldex G-TA or B-TA column (30m×0.25mm×0.12μm, Astec).

With AFL210 recombinant BVMO from Aspergillus flavus NRRL3357 in methanol, Time= 2h, T= 20 °C , pH= 8, Enzymatic reaction, Baeyer-Villiger Ketone Oxidation, Reagent/catalyst, regioselective reaction Ferroni; Smit; Opperman; Journal of Molecular Catalysis B: Enzymatic; vol. 107; (2014); p. 47 - 54 View in Reaxys

23 %Chromat.

4.2 General procedure for Baeyer-Villiger oxidation General procedure: In a two-necked 25 mL round-bottom flask was charged with L-BIOX (0.01 mmol, 1.2 mg), a ketone (1 mmol), and benzene (2 mL) before addition of benzaldehyde (3 mmol, 306 μL) and benzene (1 mL). After purging with O2 gas, the mixture was allowed to stir at 25 °C in a water bath attached with a gas bag filled with O2 gas (1 atm). After appropriate reaction time, to the reaction mixture was added dodecane followed by filtration through a short plug of Celite and MgSO4 to remove a catalyst and the filtrate was analyzed by GC or 1H NMR. Spectral properties of products (2a, 2b, 2d, 2g, 2h) were identical with those of commercial (TCI, nacalai tesque, Kanto) authentic sample. Spectral properties of products (2c, 2e, 2f, 2i) were identical with those of authentic sample synthesized according to the reported procedure.42 Spectral property of 2cγ was identical with the reported data.43

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With oxygen, benzaldehyde in benzene, Time= 3h, T= 25 °C , p= 760.051Torr , Baeyer-Villiger Ketone Oxidation, regioselective reaction Mandai, Kyoko; Hanata, Minae; Mitsudo, Koichi; Mandai, Hiroki; Suga, Seiji; Hashimoto, Hideki; Takada, Jun; Tetrahedron; vol. 71; nb. 50; (2015); p. 9403 - 9407 View in Reaxys With dihydrogen peroxide in neat (no solvent), Time= 6h, T= 20 °C , Green chemistry, Baeyer-Villiger Ketone Oxidation, Catalytic behavior Saikia, Pallab Kumar; Sarmah, Podma Pollov; Borah, Bibek Jyoti; Saikia, Lakshi; Saikia, Kokil; Dutta, Dipak Kumar; Green Chemistry; vol. 18; nb. 9; (2016); p. 2843 - 2850 View in Reaxys Biotransformations and Steady-state kinetics General procedure: Biotransformations were performed in amber glass vials (40 mL) in a total reaction volume of 1 mL. Wholecell (WC) and cell-free extract (CFE) biotransformations were performed aspreviously described [7]. Reactions with purified BVMO were performed in 100 mM Tris-HCl buffer (pH 8) containing 2 μM BVMO, 0.5 U BmGDH, 100 mM glucose, 0.3 mMNADP+ and 10 mM substrate. Reactions were maintained at 20°C with shaking (200 rpm),where after they were extracted using an equal volume (2 x 0.5 mL) ethyl acetate containing either 2 mM 1-undecanol or 3-octanol as internal standard. GC-FID (and GC-MS forproduct identification) was performed on a Finnigan Trace GC ultra (ThermoScientific)equipped with a FactorFour VF-5ms column (60 m x 0.32 mm x 0.25 μm, Varian). Steadystatekinetics were performed by monitoring the oxidation of NADPH spectrophotometericallyat 340 nm (γ340 = 6.22 mM-1.cm-1) or 370 nm(γ370 = 2.70 mM-1.cm-1). To investigate optimal pH, temperature, stability and effect of organic solvents, reactions typically contained2 μM BVMO, 0.3 mM NADPH, 1 mM phenylacetone, 1percent (v/v) methanol (100 mMTris-HCl, pH 8; 25°C).

With D-Glucose, Aspergillus flavus Baeyer-Villiger monooxygenaseAFL838 , nicotinamide adenine dinucleotide phosphate in aq. buffer, Time= 8h, T= 20 °C , pH= 8, Enzymatic reaction, Baeyer-Villiger Ketone Oxidation, Catalytic behavior, Kinetics, Reagent/catalyst, regioselective reaction Ferroni, Felix Martin; Tolmie, Carmien; Smit, Martha Sophia; Opperman, Diederik Johannes; PLoS ONE; vol. 11; nb. 7; (2016); Art.No: E0160186 View in Reaxys With dihydrogen peroxide in 1,4-dioxane, T= 100 °C , Baeyer-Villiger Ketone Oxidation Yakabi, Keiko; Mathieux, Thibault; Milne, Kirstie; López-Vidal, Eva M.; Buchard, Antoine; Hammond, Ceri; ChemSusChem; vol. 10; nb. 18; (2017); p. 3652 - 3659 View in Reaxys O

O

O

O

I O O

Rx-ID: 36691246 View in Reaxys 7/238 Yield 38 %

Conditions & References With acridine, palladium diacetate in acetic anhydride, acetic acid, Time= 5h, T= 100 °C , Reagent/catalyst Cook, Amanda K.; Emmert, Marion H.; Sanford, Melanie S.; Organic Letters; vol. 15; nb. 21; (2013); p. 5428 - 5431 View in Reaxys

29 %Chromat.

With acetic anhydride, acetic acid, Time= 24h, T= 104 °C , Reagent/catalyst Majeed, Maitham H.; Shayesteh, Payam; Wallenberg, L. Reine; Persson, Axel R.; Johansson, Niclas; Ye, Lei; Schnadt, Joachim; Wendt, Ola F.; Chemistry - A European Journal; vol. 23; nb. 35; (2017); p. 8457 - 8465 View in Reaxys

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O O O

O

I O

O

Rx-ID: 36691247 View in Reaxys 8/238 Yield

Conditions & References

78 %

Stage 1: With 6-fluoropyridine-2-carboxylic acid, palladium diacetate, acetic anhydride, acetic acid, Time= 0.00416667h, T= 20 °C Stage 2:Time= 309h, T= 100 °C , Sealed tube, Catalytic behavior, Mechanism, Reagent/catalyst Valderas, Carolina; Naksomboon, Kananat; Fernández-Ibáñez, M. Ángeles; ChemCatChem; vol. 8; nb. 20; (2016); p. 3213 - 3217 View in Reaxys

20.9 %

With pyridine, palladium diacetate, acetic acid in Hexafluorobenzene, acetic anhydride, Time= 5h, T= 100 °C , Sealed tube, Kinetics, Reagent/catalyst Cook, Amanda K.; Sanford, Melanie S.; Journal of the American Chemical Society; vol. 137; nb. 8; (2015); p. 3109 - 3118 View in Reaxys

12 %Chromat.

With palladium diacetate in acetic anhydride, acetic acid, T= 100 °C Cook, Amanda K.; Emmert, Marion H.; Sanford, Melanie S.; Organic Letters; vol. 15; nb. 21; (2013); p. 5428 - 5431 View in Reaxys

31 %Chromat.

With C16H18I2N4OPd, acetic anhydride, acetic acid, Time= 24h, T= 95 °C , Sealed tube, Reagent/catalyst Desai, Sai Puneet; Mondal, Moumita; Choudhury, Joyanta; Organometallics; vol. 34; nb. 12; (2015); p. 2731 - 2736 View in Reaxys

32 %Chromat.

With acetic anhydride, acetic acid, Time= 24h, T= 104 °C , Reagent/catalyst Majeed, Maitham H.; Shayesteh, Payam; Wallenberg, L. Reine; Persson, Axel R.; Johansson, Niclas; Ye, Lei; Schnadt, Joachim; Wendt, Ola F.; Chemistry - A European Journal; vol. 23; nb. 35; (2017); p. 8457 - 8465 View in Reaxys With 3-methyl-2-(phenylthio)butanoic acid, palladium diacetate, acetic anhydride, acetic acid, Time= 3h, T= 100 °C , Heck Reaction Naksomboon, Kananat; Valderas, Carolina; Gómez-Martínez, Melania; Álvarez-Casao, Yolanda; Fernández-Ibáñez, M. Ángeles; ACS Catalysis; vol. 7; nb. 9; (2017); p. 6342 - 6346 View in Reaxys

–

O

2

O

O Cu

O

2+

Rx-ID: 44495064 View in Reaxys 9/238 Yield

Conditions & References 3.5. Benzene oxidation in non-acidic media The lack of benzene oxidation in HTFA (see above) could resultfrom the failure of the Rh complexes to mediate benzene C– Hactivation in trifluoroacetic acid. We speculated that non-acidicsolvents might allow arene functionalization chemistry (Eq. (3)).A 0.5 molpercent solution of 7 or 11 in benzene with 100 equivalents ofcopper (II) acetate was heated to 150C and 180C for 4 h. Analysisby GC/MS revealed no benzene functionalization at 150C. How-ever, at 180C the production of biphenyl and a minor quantity ofPhOAc was observed when using Cu(OAc)2. Control experimentsat 180C without rhodium catalyst produced the same quantity ofphenyl acetate; however, no biphenyl was observed. The formationof PhOAc presumably is due to reaction with Cu(OAc)2. This wasconfirmed by running a control reaction in toluene and producingsignificantly more benzylic acetate than tolylacetate (see Support-ing information, Scheme S1). The production of biphenyl was alsoobserved with catalyst 4, 7, 11 and [Rh(-TFA)(2-C2H4)2]2in sim-ilar yields.

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, Time= 24h, T= 180 °C , Catalytic behavior Webster-Gardiner, Michael S.; Piszel, Paige E.; Fu, Ross; McKeown, Bradley A.; Nielsen, Robert J.; Goddard, William A.; Gunnoe, T. Brent; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 381 - 388 View in Reaxys

–O

O

O

2

O

Cu 2+

Rx-ID: 44495065 View in Reaxys 10/238 Yield

Conditions & References 3.5. Benzene oxidation in non-acidic media The lack of benzene oxidation in HTFA (see above) could resultfrom the failure of the Rh complexes to mediate benzene C– Hactivation in trifluoroacetic acid. We speculated that non-acidicsolvents might allow arene functionalization chemistry (Eq. (3)).A 0.5 molpercent solution of 7 or 11 in benzene with 100 equivalents ofcopper (II) acetate was heated to 150C and 180C for 4 h. Analysisby GC/MS revealed no benzene functionalization at 150C. How-ever, at 180C the production of biphenyl and a minor quantity ofPhOAc was observed when using Cu(OAc)2. Control experimentsat 180C without rhodium catalyst produced the same quantity ofphenyl acetate; however, no biphenyl was observed. The formationof PhOAc presumably is due to reaction with Cu(OAc)2. This wasconfirmed by running a control reaction in toluene and producingsignificantly more benzylic acetate than tolylacetate (see Support-ing information, Scheme S1). The production of biphenyl was alsoobserved with catalyst 4, 7, 11 and [Rh(-TFA)(2-C2H4)2]2in sim-ilar yields.

With C12H16F6O4Rh2, Time= 24h, T= 180 °C , Catalytic behavior, Reagent/catalyst Webster-Gardiner, Michael S.; Piszel, Paige E.; Fu, Ross; McKeown, Bradley A.; Nielsen, Robert J.; Goddard, William A.; Gunnoe, T. Brent; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 381 - 388 View in Reaxys

O

O HO

O

Rx-ID: 46960017 View in Reaxys 11/238 Yield

Conditions & References

33 %, 23 %

With dihydrogen peroxide in 1,2-dichloro-ethane, Time= 24h, T= 80 °C , Baeyer-Villiger Ketone Oxidation, regioselective reaction Jennings, John A.; Parkin, Sean; Munson, Eric; Delaney, Sean P.; Calahan, Julie L.; Isaacs, Mark; Hong, Kunlun; Crocker, Mark; RSC Advances; vol. 7; nb. 42; (2017); p. 25987 - 25997 View in Reaxys

O

O

Cl

O

HO

Rx-ID: 693050 View in Reaxys 12/238 Yield 99 %

Conditions & References 4.2. General procedure for O-acylation of phenols in TfOH General procedure: Phenol (0.28 mmol) and acyl chloride (0.84 mmol, 3 equiv) were dissolved in 1percent TfOH/CH3CN (1 ml) at room temperature. The reaction mixture was stirred at same temperature for an hour, then poured into cold water and ethyl acetate. The organic layer was washed with 1 M HCl, saturated NaHCO3, and saturated NaCl, and dried over MgSO4, then filtered. The filtrate was concentrated to afford O-acylated products. All spectral data were identical with the literatures.[27] , 27(a) , 27(b) , 27(c) , 27(d) , 27(e) , 27(f) , 27(g) and 27(h)

With trifluorormethanesulfonic acid in acetonitrile, Time= 1h, T= 20 °C

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Murashige, Ryo; Hayashi, Yuka; Ohmori, Syo; Torii, Ayuko; Aizu, Yoko; Muto, Yasuyuki; Murai, Yuta; Oda, Yuji; Hashimoto, Makoto; Tetrahedron; vol. 67; nb. 3; (2011); p. 641 - 649 View in Reaxys 99 %

1.1 : 1) Preparation of phenyl acetate To a three-necked flask was added 14.1 g (0.15 mol) of phenol, 14.13 g (0.18 mol) of acetyl chloride and 40 ml of cyclohexane, reacted at room temperature for 2-3h. At the end of the reaction, sodium bicarbonate was added to adjust the pH of 8, organic phase was collected, and dried over anhydrous sodium sulfate and the product was obtained as a pale yellow oily liquid phenyl acetate 20.2 g (yield 99percent). in cyclohexane, T= 20 °C , Solvent, Temperature Patent; Shanghai Institute of Technology; Yao, Zhiyi; Li, Caihong; Su, Kun; Zong, Haoqiang; Wu, Yunlong; Li, Zhengfeng; Li, Xing; (7 pag.); CN104529726; (2016); (B) Chinese View in Reaxys

98 %

With montmorillonite K-10 in dichloromethane, Time= 2h, Ambient temperature Li, Tong-Shuang; Li, Ai-Xiao; Journal of the Chemical Society - Perkin Transactions 1; nb. 12; (1998); p. 1913 - 1917 View in Reaxys

98 %

With Fe/SWCNTs, Time= 0.3h, T= 20 °C Sharghi, Hashem; Jokar, Mahboubeh; Doroodmand, Mohammad Mahdi; Advanced Synthesis and Catalysis; vol. 353; nb.

2-3; (2011); p. 426 - 442 View in Reaxys

98 %

General procedure: In a typical experimental procedure, to a mixture of alcohol/phenol (1mmol) and acetic anhydride (1.0mmol) or acyl chloride (1.0mmol) in dichloromethane solvent (2vol) or without solvent, Zn(OTf)2 (0.1molpercent) was added. The reaction mixture was stirred at room temperature for the specified time. Completion of reaction was monitored by TLC, after quenching with a saturated solution of NaHCO3 and the products were extracted in to dichloromethane (3×10mL). The combined organic layer was washed with water, dried over anhydrous Na2SO4, and concentrated in vacuum to obtain the product. #10; With zinc trifluoromethanesulfonate in dichloromethane, Time= 0.00277778h, T= 20 °C , Solvent Kumar, N. Uday; Reddy, B. Sudhakar; Reddy, V. Prabhakar; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 55; nb. 4; (2014); p. 910 - 912 View in Reaxys

97 %

With 1,4-diaza-bicyclo[2.2.2]octane, Time= 0.133333h Hajipour; Mazloumi; Synthetic Communications; vol. 32; nb. 1; (2002); p. 23 - 30 View in Reaxys

95 %

With ZnAl2O4 nanoparticles, Time= 0.6h, T= 20 °C , Neat (no solvent) Farhadi, Saeid; Panahandehjoo, Somayeh; Applied Catalysis A: General; vol. 382; nb. 2; (2010); p. 293 - 302 View in Reaxys

94 %

With zinc(II) oxide, Time= 0.25h, T= 20 °C Hosseini Sarvari, Mona; Sharghi, Hashem; Tetrahedron; vol. 61; nb. 46; (2005); p. 10903 - 10907 View in Reaxys

92 %

With tetrabutyl-ammonium chloride, sodium hydroxide in dichloromethane, water, Time= 0.0833333h, T= 0 °C Simion, Alina Marieta; Hashimoto, Iwao; Mitoma, Yoshiharu; Egashira, Naoyoshi; Simion, Cristian; Synthetic Communications; vol. 42; nb. 6; (2012); p. 921 - 931 View in Reaxys

90 %

With sodium hydride in tetrahydrofuran, Time= 1h, T= 20 °C Wiles, Charlotte; Watts, Paul; Haswell, Stephen J.; Pombo-Villar, Esteban; Tetrahedron; vol. 59; nb. 51; (2003); p. 10173 10179 View in Reaxys

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90 %

With zinc(II) oxide, Time= 1h, T= 20 °C Tamaddon, Fatemeh; Amrollahi, Mohammad Ali; Sharafat, Leily; Tetrahedron Letters; vol. 46; nb. 45; (2005); p. 7841 7844 View in Reaxys

90 %

With titanium(IV) oxide, Time= 0.166667h, T= 25 °C Pasha, Mohamed Afzal; Manjula, Krishnappa; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 47; nb. 4; (2008); p. 597 - 600 View in Reaxys

90 %

General procedure for O-acetylation of alcohols and phenols using HAP–Cu2O General procedure: A mixture of alcohol or phenol (1 mmol), acetyl chloride(1 mmol), hydroxyapatite –Cu2O (0.1 g) in acetonitrilewas taken in a round-bottom flask and stirred at 50 °C foran appropriate time. On completion (monitored by TLC),the reaction mixture was cooled to room temperature andfiltered. The residue was washed with water followed byEtOAc (3 × 10 mL).

The product was obtained after theremoval of solvent under reduced pressure followed bycrystallization from pet ether or EtOAc:pet ether or passingthrough column of silica and elution with EtOAc:pet ether.

With hydroxyapatite supported copper(I) oxide in acetonitrile, Time= 0.5h, T= 50 °C Gupta, Manjulla; Gupta, Monika; Journal of the Iranian Chemical Society; vol. 13; nb. 2; (2016); p. 231 - 241 View in Reaxys

89 %

With cesium fluoride in acetonitrile, T= 20 °C Shah, Syed Tasadaque A; Khan, Khalid M; Heinrich, Angelica M; Choudhary, M.Iqbal; Voelter; Tetrahedron Letters; vol.

43; nb. 47; (2002); p. 8603 - 8606 View in Reaxys

89 %

With cesium fluoride in acetonitrile, T= 20 °C Shah, Syed Tasadaque Ali; Khan, Khalid Mohammed; Hussain, Hidayat; Anwar, Muhammad Usman; Fecker, Miriam; Voelter, Wolfgang; Tetrahedron; vol. 61; nb. 27; (2005); p. 6652 - 6656 View in Reaxys

88 %

With carbon-silica composite from starch (7.5 molpercent SO3H), Time= 3.5h, T= 60 °C , solvent-free conditions Gupta, Princy; Paul, Satya; Green Chemistry; vol. 13; nb. 9; (2011); p. 2365 - 2372 View in Reaxys

80 %

in dichloromethane, Time= 3h, T= 25 °C , ultrasound, Product distribution, Further Variations: Solvents, Reaction partners, Temperatures, without ultrasound; reaction time Rama; Pasha; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 41; nb. 12; (2002); p. 2604 2605 View in Reaxys

77 %

in neat (no solvent), T= 150 °C , Microwave irradiation Kim, Bo Ram; Sung, Gi Hyeon; Lee, Sang-Gyeong; Yoon, Yong Jin; Tetrahedron; vol. 69; nb. 15; (2013); p. 3234 - 3237 View in Reaxys

76 %

in neat (no solvent), Time= 1h, T= 150 °C Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Kim, Jeum-Jong; Yoon, Yong-Jin; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3410 - 3414 View in Reaxys

40 %

With zinc(II) chloride, Time= 2.5h, T= 30 °C , Neat (no solvent) Yadav, Prakrati; Lagarkha, Rekha; Balla, Zahoor Ahmad; Asian Journal of Chemistry; vol. 22; nb. 7; (2010); p. 5155 5158 View in Reaxys

20 %

Stage 1: With aluminum (III) chloride in tetrahydrofuran, Time= 1h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 1h, Reflux

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Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Yoon, Hyo Jae; Lee, Sang-Gyeong; Yoon, Yong-Jin; Synlett; vol. 25; nb. 13; (2014); p. 1909 - 1915; Art.No: ST-2014-U0361-L View in Reaxys in acetonitrile, T= 0 - 25 °C , also in the presence of NEt4Cl, Kinetics, Mechanism Kevill, Dennis, N.; Kim, Chang-Bae; Bulletin de la Societe Chimique de France; nb. 2; (1988); p. 383 - 390 View in Reaxys With magnesium, benzene Spassow; Chemische Berichte; vol. 75; (1942); p. 779; 35 Chimija <1938/39> 289 View in Reaxys Cahours; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 39; (1854); p. 257; Justus Liebigs Annalen der Chemie; vol. 92; (1854); p. 316 View in Reaxys Suzuki, Hitomi; Tatsumi, Atsuo; Ishibashi, Taro; Mori, Tadashi; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1995); p. 339 - 344 View in Reaxys With zinc Schiaparelli; Gazzetta Chimica Italiana; vol. 11; (1881); p. 69; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1881); p. 539 View in Reaxys Reaktion ueber mehrere Stufen Hoeflake; Recueil des Travaux Chimiques des Pays-Bas; vol. 36; (1917); p. 30 View in Reaxys With tin(IV) chloride Perkin; Journal of the Chemical Society; vol. 119; (1921); p. 1288 View in Reaxys Adickes; Brunnert; Luecker; Journal fuer Praktische Chemie (Leipzig); vol. <2>130; (1931); p. 163,164 View in Reaxys 100 % Chromat.

With triethylamine in diethyl ether, Time= 1h, Ambient temperature Strazzolini, Paolo; Verardo, Giancarlo; Giumanini, Angelo G.; Journal of Organic Chemistry; vol. 53; nb. 14; (1988); p.

3321 - 3325 View in Reaxys in benzene, Heating Jiang, Xi-Kui; Hui, Yong-Zheng; Fan, Wei-Qiang; Journal of the American Chemical Society; vol. 106; nb. 13; (1984); p.

3839 - 3843 View in Reaxys Cahours; Justus Liebigs Annalen der Chemie; vol. 92; (1854); p. 315 View in Reaxys 12-15 stdg. Behandeln von Aluminium-dichlorid-phenolat Norris; Sturgis; Journal of the American Chemical Society; vol. 61; (1939); p. 1413,1416 View in Reaxys With sodium hydroxide, tetrabutyl-ammonium chloride in dichloromethane, Time= 0.0833333h, T= 0 °C , Product distribution, Further Variations: Temperatures, Reagents, Solvents Hashimoto, Iwao; Kawaji, Takatoshi; Mitoma, Yoshiharu; Simion, Alina M.; Semion, Cristian; Ishimoto, Keiko; Prakash, G.K. Surya; Olah, George A.; Tashiro, Masashi; Revue Roumaine de Chimie; vol. 49; nb. 2; (2004); p. 149 - 155 View in Reaxys

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82 %Chromat.

With zinc(II) oxide, Time= 0.0833333h, T= 20 °C Tayebee, Reza; Cheravi, Fatemeh; Mirzaee, Mehdi; Amini, Mojtaba M.; Chinese Journal of Chemistry; vol. 28; nb. 7; (2010); p. 1247 - 1252 View in Reaxys With pyridine in dichloromethane China Raju; Nageswara Rao; Suman; Yogeeswari; Sriram; Shaik, Thokhir Basha; Kalivendi, Shasi Vardhan; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 10; (2011); p. 2855 - 2859 View in Reaxys With pyridine in dichloromethane Kumar, J. Ashok; Saidachary; Mallesham; Sridhar; Jain, Nishant; Kalivendi, Shashi Vardhan; Rao, V. Jayathirtha; Raju, B. China; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 389 - 402 View in Reaxys Time= 1h, Heating Singh, Satyajit; Baviskar, Ashish Triambak; Jain, Vaibhav; Mishra, Nidhi; Chand Banerjee, Uttam; Bharatam, Prasad V.; Tikoo, Kulbhushan; Singh Ishar, Mohan Paul; MedChemComm; vol. 4; nb. 9; (2013); p. 1257 - 1266 View in Reaxys 4.2 General procedure for Fries rearrangement and catalyst preparation General procedure: Catalyst (FSG) was purchased from Fluorous Technologies Inc. and used without further purification. Its synthesis procedure is reported by Curran et al. [24]. General procedure for Fries rearrangement was done by adding FSG to aryl ester at the ambient temperatures. Before adding FSG to reaction mixture, aryl esters were obtained by in situ formation through the reaction of acyl chloride derivatives and phenol derivatives. Thus, to a 100ml round bottom flask stirring by a magnetic bar 10mmol of phenols was added and then, 10mmol of acyl chloride derivatives (for catechols 20mmol) was added dropwise and allowed to react at room temperature. After 30min, temperature was raised to remove HCl from reaction mixture. Then 1g of FSG was added to reaction mixture at ambient temperature. After 4h heating at appropriate temperature in oil bath, the reaction mixture was cooled to room temperature and washed with dichloromethane. The catalyst was separated by filtration. The solvent was removed by rotary evaporator and resulting mixture was separated by column chromatography (stationary phase: silica-gel, eluent:hexane:ethyl acetate) and purified by recrystallization. All isolated products successfully gave related spectral data of IR, NMR, and mass spectrometers. in neat (no solvent), Time= 0.5h, T= 20 °C Ghaffarzadeh, Mohammad; Ahmadi, Maryam; Journal of Fluorine Chemistry; vol. 160; (2014); p. 77 - 81 View in Reaxys

O

O

O

O

HO

Rx-ID: 851012 View in Reaxys 13/238 Yield 99 %

Conditions & References With 1,4-diaza-bicyclo[2.2.2]octane in neat (no solvent), Time= 0.183333h, T= 70 - 140 °C , Microwave irradiation, Catalytic behavior, Temperature, Solvent, Reagent/catalyst, Time Kumar, Manoj; Bagchi, Sourav; Sharma, Anuj; New Journal of Chemistry; vol. 39; nb. 11; (2015); p. 8329 - 8336 View in Reaxys

97 %

General Procedure for the Reaction of Various Alcoholswith Vinyl Acetate General procedure: Alcohol 24 (1.0 mmol), vinyl acetate (25) (0.103 g, 1.20mmol), 1 (0.080 g, 0.10 mmol), and THF(1.0 mL) were added to a 3-mL vial. The vial was immersed in an oil bath regulated at 60 °C for 16 h.The reaction mixture was cooled to rt and then filtered. The beads collected on funnel were furtherwashed with THF (5 mL). Combined filtrate was concentrated under reduced pressure. The residue ofconcentrated filtrate afforded essentially pure products as analyzed by 1H and 13C NMR spectroscopy forsubstrates in Table 1, entries 1-4. In cases the reactions were incomplete under the given conditions, theproducts were purified using silica gel column chromatography with hexane as the eluent.

With Rasta resin-(1,5,7-triazabicyclo[4.4.0]dec-5-ene)[RR-TBD] in tetrahydrofuran, T= 20 - 60 °C

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Yang, Yun-Chin; Leung, Dennis Y.C.; Toy, Patrick H.; Synlett; vol. 24; nb. 14; (2013); p. 1870 - 1874; Art.No: ST-2013W0412-L View in Reaxys 80 %

With 4 A molecular sieve, tetrabutylammonium tricarbonylnitrosylferrate in hexane, Time= 24h, T= 80 °C Magens, Silja; Ertelt, Melanie; Jatsch, Anja; Plietker, Bernd; Organic Letters; vol. 10; nb. 1; (2008); p. 53 - 56 View in Reaxys

63 %

With pseudomonas fuorescens lipase immobilized on multiwall carbon nano-tubes, Time= 12h, T= 50 °C , Green chemistry Badgujar, Kirtikumar Chandulal; Sasaki, Takehiko; Bhanage, Bhalchandra Mahadeo; RSC Advances; vol. 5; nb. 68; (2015); p. 55238 - 55251 View in Reaxys

7.4 %

With bis{[2-(dimethylaminomethyl)phenyl]di-n-butyltin(IV)} oxide, Time= 45h, T= 30 °C Padelkova, Zdenka; Weidlich, Tomas; Kolarova, Lenka; Eisner, Ales; Cisarova, Ivana; Zevaco, Thomas A.; Ruzicka, Ales; Journal of Organometallic Chemistry; vol. 692; nb. 25; (2007); p. 5633 - 5645 View in Reaxys With sulfuric acid Patent; Consort. elektrochem. Ind.; DE578378; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 920 View in Reaxys in tetrahydrofuran, cyclohexane, T= 40 °C , adsorbed Chromobacterium viscosum lipase, Rate constant Nicolosi; Piatelli; Sanfilippo; Tetrahedron; vol. 48; nb. 12; (1992); p. 2477 - 2482 View in Reaxys in tetrahydrofuran, cyclohexane, T= 40 °C , initial rate of acetylation; Chromobacterium viscosum lipase adsorbed on Hyflo Super Cel; other hydroxybenzenes Lambusta, Daniela; Nicolosi, Giovanni; Piattelli, Mario; Sanfilippo, Claudia; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 1; (1993); p. 58 - 60 View in Reaxys With silver trifluoroacetate, triethylamine, (triphenylphosphine)gold(I) chloride, T= 50 °C Nakamura, Aki; Tokunaga, Makoto; Tetrahedron Letters; vol. 49; nb. 23; (2008); p. 3729 - 3732 View in Reaxys 4.14. General procedure for the lipase-catalyzed transesterification of phenol 11 or o-methoxyphenol 12 General procedure: After exhaustive drying of THF, substrate, and lipase under 0.1mmHg conditions, substrate 11 (50mg, 0.53mmol) or 12 (50mg, 0.40mmol), vinyl acetate (33.5mg, 0.39mmol), and the lipase (dry MeitoQLM, 25mg) in i-Pr2O (0.75mL) with molecular sieves 4Å were stirred for approximately 30min at 35°C. The reaction was followed by GC using a column of DB5 (detector and injection temperature, 280°C; column temperature, 100°C; carrier gas, He; linear velocity: 30cm/s, FID detector). Under these conditions the retention times of 11, 12, 13, and 14 were 3.6, 5.8, 5.1, and 14.0min, respectively.

Conversion was assessed by GC. With lipase from Alcaligenessp. in tetrahydrofuran, di-isopropyl ether, Time= 2h, T= 35 °C , p= 0.1Torr , Molecular sieve, Enzymatic reaction Kitayama, Takashi; Isomori, Sachiko; Nakamura, Kaoru; Tetrahedron Asymmetry; vol. 24; nb. 11; (2013); p. 621 - 627 View in Reaxys

O

O

OH

O HO

Rx-ID: 8825188 View in Reaxys 14/238

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Yield

Conditions & References

1.29 mmol, 0.08 mmol, 0.08 mmol

With oxygen, palladium diacetate, bis(acetylacetonato)dioxidomolybdenum(VI), Time= 4h, T= 130 °C , p= 7600Torr Okamoto, Makoto; Yamaji, Teizo; Chemistry Letters; nb. 3; (2001); p. 212 - 213 View in Reaxys With phosphomolybdic acid hydrate, water, oxygen, palladium diacetate, Time= 4h, T= 130 °C , p= 7600Torr , Product distribution, Further Variations: Reagents Okamoto, Makoto; Watanabe, Midori; Yamaji, Teizo; Journal of Organometallic Chemistry; vol. 664; nb. 1-2; (2002); p. 59 65 View in Reaxys 1 : Table1: General procedure A 45-mL Hastelloy C-276 vessel was charged with a teflon stirbar, the specified molpercent of Pd(OAc)2, as indicated in Table2 (it is easiest to use a stock solution of Pd(OAc)2/AcOH), a total of 12.1 mL of AcOH, and benzene (626μl, 7 mmol). The reactor was sealed, pressurized to either 11 atm or 111 atm of 9percent O2/N2 (effectively 1 atm of O2 or 10atm of O2), and then heated to 100 °C and stirred vigorously for 10 h. The vessel was then allowed to cool to room temperature and the reaction mixture was analyzed by GC analysis using chlorobenzene as an internal standard. TONs are reported based on mmol PhOAc+mmol PhOH +mmol Ph−Ph. Ratios of (PhOAc+PhOH):Ph−Ph are based on mmol of products.

With oxygen, palladium diacetate, Time= 10h, T= 100 °C , p= 760.051Torr , Catalytic behavior, Pressure Zultanski, Susan L.; Stahl, Shannon S.; Journal of Organometallic Chemistry; vol. 793; (2015); p. 263 - 268; Art.No: 18950 View in Reaxys

O

O

O

O

HO

Rx-ID: 10450911 View in Reaxys 15/238 Yield

Conditions & References

99 %

With iodine, Time= 0.0833333h, T= 85 - 90 °C Ahmed, Naseem; van Lier, Johan E.; Tetrahedron Letters; vol. 47; nb. 30; (2006); p. 5345 - 5349 View in Reaxys

95 %

With aluminum triflate, Time= 0.116667h, T= 20 °C Kamal, Ahmed; Khan, M. Naseer A.; Reddy, K. Srinivasa; Srikanth; Krishnaji; Tetrahedron Letters; vol. 48; nb. 22; (2007); p. 3813 - 3818 View in Reaxys

93 %

With 1,4-diaza-bicyclo[2.2.2]octane in neat (no solvent), Time= 0.183333h, T= 60 - 140 °C , Microwave irradiation Kumar, Manoj; Bagchi, Sourav; Sharma, Anuj; New Journal of Chemistry; vol. 39; nb. 11; (2015); p. 8329 - 8336 View in Reaxys

O

O

OH

O

Rx-ID: 22842189 View in Reaxys 16/238 Yield

Conditions & References With methanol, oxygen, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys With oxygen, isopropyl alcohol, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English

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View in Reaxys With cyclohexane, oxygen, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys With oxygen, cyclohexene, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys With oxygen, cyclohexene, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys With oxygen, acetaldehyde, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys With ethanol, oxygen, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys With ethanol, oxygen, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys With formic acid, oxygen, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys With oxygen, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys With oxygen, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys With oxygen, iso-butanol, Conversion of starting material Patent; Tosoh Corporation; US6342620; (2002); (B1) English View in Reaxys Table3: General procedure General procedure: An oven-dried Ace pressure tube (9 mL, bushing type, front seal, 20.3 cmL x 13 mm O.D.) was charged with a teflon stirbar, 100 μl of a 0.00012 M Pd(OAc)2/AcOH stock solution (stock solution: 26.9 mg in 10 mL of AcOH; 0.0012 mmol Pd(OAc)2 per reaction), and 1.9 mL of AcOH. The tube was capped with a septum and purged for 2 min with an oxygen balloon, while stirring (exception: for entry 8, N2 was used in place of O2). Benzene (108 μl, 1.2 mmol) was added via syringe, followed by the specified quantity of the NOx source, via syringe. The rubber septum was removed, quickly capped with a Teflon cap, and stirred vigorously in a 100 °C oil bath for 24 h (the oil bath level is the same height as the solution level of the reaction). The pressure tube was then allowed to cool to room temperature and the reaction mixture was analyzed by GC analysis using chlorobenzene as an internal standard. TONs are reported solely based on mmol PhOAc. Ratios of PhOAc:PhNO2 are based on mmol of products.*Entry 4 is the average of 4 runs: Run 1: TON=137; 28:1 PhOAc:PhNO2 Run 2: TON=136; 26:1 PhOAc:PhNO2 Run 3: TON=121; 30:1 PhOAc:PhNO2 Run 4: TON=149; 21:1 PhOAc:PhNO2 Standard deviation for TON: 9.9 Standard deviation for PhOAc:PhNO2 ratio: 3.3 With oxygen, nitric acid, palladium diacetate, Time= 24h, T= 100 °C , p= 760.051Torr , Sealed tube, Catalytic behavior

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Zultanski, Susan L.; Stahl, Shannon S.; Journal of Organometallic Chemistry; vol. 793; (2015); p. 263 - 268; Art.No: 18950 View in Reaxys

O

O

O

OH

O

N O

Rx-ID: 40926625 View in Reaxys 17/238 Yield

Conditions & References Table3: General procedure General procedure: An oven-dried Ace pressure tube (9 mL, bushing type, front seal, 20.3 cmL x 13 mm O.D.) was charged with a teflon stirbar, 100 μl of a 0.00012 M Pd(OAc)2/AcOH stock solution (stock solution: 26.9 mg in 10 mL of AcOH; 0.0012 mmol Pd(OAc)2 per reaction), and 1.9 mL of AcOH. The tube was capped with a septum and purged for 2 min with an oxygen balloon, while stirring (exception: for entry 8, N2 was used in place of O2). Benzene (108 μl, 1.2 mmol) was added via syringe, followed by the specified quantity of the NOx source, via syringe. The rubber septum was removed, quickly capped with a Teflon cap, and stirred vigorously in a 100 °C oil bath for 24 h (the oil bath level is the same height as the solution level of the reaction). The pressure tube was then allowed to cool to room temperature and the reaction mixture was analyzed by GC analysis using chlorobenzene as an internal standard. TONs are reported solely based on mmol PhOAc. Ratios of PhOAc:PhNO2 are based on mmol of products.*Entry 4 is the average of 4 runs: Run 1: TON=137; 28:1 PhOAc:PhNO2 Run 2: TON=136; 26:1 PhOAc:PhNO2 Run 3: TON=121; 30:1 PhOAc:PhNO2 Run 4: TON=149; 21:1 PhOAc:PhNO2 Standard deviation for TON: 9.9 Standard deviation for PhOAc:PhNO2 ratio: 3.3 With oxygen, nitric acid, palladium diacetate, Time= 24h, T= 100 °C , p= 760.051Torr , Sealed tube, Catalytic behavior, Reagent/catalyst Zultanski, Susan L.; Stahl, Shannon S.; Journal of Organometallic Chemistry; vol. 793; (2015); p. 263 - 268; Art.No: 18950 View in Reaxys Table3: General procedure General procedure: An oven-dried Ace pressure tube (9 mL, bushing type, front seal, 20.3 cmL x 13 mm O.D.) was charged with a teflon stirbar, 100 μl of a 0.00012 M Pd(OAc)2/AcOH stock solution (stock solution: 26.9 mg in 10 mL of AcOH; 0.0012 mmol Pd(OAc)2 per reaction), and 1.9 mL of AcOH. The tube was capped with a septum and purged for 2 min with an oxygen balloon, while stirring (exception: for entry 8, N2 was used in place of O2). Benzene (108 μl, 1.2 mmol) was added via syringe, followed by the specified quantity of the NOx source, via syringe. The rubber septum was removed, quickly capped with a Teflon cap, and stirred vigorously in a 100 °C oil bath for 24 h (the oil bath level is the same height as the solution level of the reaction). The pressure tube was then allowed to cool to room temperature and the reaction mixture was analyzed by GC analysis using chlorobenzene as an internal standard. TONs are reported solely based on mmol PhOAc. Ratios of PhOAc:PhNO2 are based on mmol of products.*Entry 4 is the average of 4 runs: Run 1: TON=137; 28:1 PhOAc:PhNO2 Run 2: TON=136; 26:1 PhOAc:PhNO2 Run 3: TON=121; 30:1 PhOAc:PhNO2 Run 4: TON=149; 21:1 PhOAc:PhNO2 Standard deviation for TON: 9.9 Standard deviation for PhOAc:PhNO2 ratio: 3.3 With nitric acid, palladium diacetate, Time= 24h, T= 100 °C , p= 760.051Torr , Sealed tube, Inert atmosphere, Catalytic behavior Zultanski, Susan L.; Stahl, Shannon S.; Journal of Organometallic Chemistry; vol. 793; (2015); p. 263 - 268; Art.No: 18950 View in Reaxys

F O

HO

Si

F

OH

O

O

O F

S O

O

O

Rx-ID: 41027911 View in Reaxys 18/238 Yield

Conditions & References Typical procedure for O-arylation of aliphatic carboxylic acids with arynes: General procedure: Kobayashi silylaryl triflate 1 (0.68 mmol) and aliphatic carboxylic acid 2 (3.4 mmol) in acetonitrile(4.0 mL) was added sodium hydroxide (80 mg, 2.0 mmol) under nitrogen atmosphere. After stirringfor 10 minutes at room temperature,

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cesium fluoride (410 mg, 2.7 mmol) was then introduced. Themixture was stirred at 80 oC for 4 h. After removal of the solvent, the residue was then purified byflash column chromatography on silica gel (eluent = petroleum ether/ethyl acetate 10:1 v/v) to givethe desired product 3.

Stage 1: With sodium hydroxide in acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere Stage 2: With cesium fluoride in acetonitrile, Time= 4h, T= 80 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst, Temperature, Overall yield = 70 percent; chemoselective reaction Wen, Chunxiao; Chen, Qian; He, Zhenwen; Yan, Xinxing; Zhang, Changyuan; Du, Zhiyun; Zhang, Kun; Tetrahedron Letters; vol. 56; nb. 40; (2015); p. 5470 - 5473 View in Reaxys

O

OH

O

O

Si

Rx-ID: 41078742 View in Reaxys 19/238 Yield

Conditions & References

88 %

With palladium diacetate, bis-[(trifluoroacetoxy)iodo]benzene, Time= 17h, T= 80 °C Gondo, Keisuke; Oyamada, Juzo; Kitamura, Tsugio; Organic Letters; vol. 17; nb. 19; (2015); p. 4778 - 4781 View in Reaxys

O O

O

O

HO

Rx-ID: 41237216 View in Reaxys 20/238 Yield

Conditions & References

96 %

With 1,4-diaza-bicyclo[2.2.2]octane in neat (no solvent), Time= 0.183333h, T= 60 - 140 °C , Microwave irradiation Kumar, Manoj; Bagchi, Sourav; Sharma, Anuj; New Journal of Chemistry; vol. 39; nb. 11; (2015); p. 8329 - 8336 View in Reaxys F

O

F

O

O

O F

HO

Rx-ID: 41237217 View in Reaxys 21/238 Yield

Conditions & References

93 %

With 1,4-diaza-bicyclo[2.2.2]octane in neat (no solvent), Time= 0.183333h, T= 60 - 140 °C , Microwave irradiation Kumar, Manoj; Bagchi, Sourav; Sharma, Anuj; New Journal of Chemistry; vol. 39; nb. 11; (2015); p. 8329 - 8336 View in Reaxys

O

O

Rx-ID: 5958487 View in Reaxys 22/238 Yield 97%

Conditions & References 2 : Preparation of a Phenyl Acetate Curative Example 2 Preparation of a Phenyl Acetate Curative A portion of the compound from EXAMPLE 1 was converted to the phenyl acetate shown above.

A 250 mL flask was charged with 37.15 g (0.11 mole) of the compound from EXAMPLE 1, 11.02 g (0.11 mole) acetic anhydride, and 0.1 g of dimethylaminopyridine.

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This mix was heated and stirred at 90° C. for two hours.

The acetic acid side product was then removed via rotary evaporation and sparge.

The final product weighted 40.5 g (97percent of theoretical yield).

An FTIR spectrum of this material revealed a small amide N-H stretch at 3318 along with prominent absorptions at 2934, 1760, 1639, 1501, 1268, 1198, 1073, 913, and 762 wavenumbers.

Patent; DESIGNER MOLECULES, INC.; US2010/113643; (2010); (A1) English View in Reaxys 88%

1 : Production of phenyl acetate EXAMPLE 1 Production of phenyl acetate In a 500 mL four-necked flask equipped with a thermometer, stirrer and reflux condenser there were charged 310 g (1.0 mole) of triphenyl phosphite, 60 g (1.0 mole) of acetic acid and 18 g (1.0 mole) of water, and the mixture was heated while stirring for one hour of reaction at 140-150° C. The reaction solution was analyzed by liquid chromatography and found to have an esterification rate of 97percent.

Next, a distillation condenser was mounted in place of the reflux condenser for distillation under reduced pressure at 20 mmHg, and the fraction with a boiling point of 90-93° C. was obtained.

The product weight was 120 g, which was a yield of 88percent.

The purity of the product was 96percent according to gas chromatography.

Patent; Yamauchi, Toshiyuki; Omichi, Masuo; Kanagawa, Eisuke; Tanino, Tomohiro; Osamura, Yoshikatsu; US2002/13491; (2002); (A1) English View in Reaxys

86%

5 : EXAMPLE 5 EXAMPLE 5 The procedure of Example 4 is repeated except that a reaction time of 4 hours at a temperature of 100° C. is employed.

Phenyl acetate is found to be produced in a yield of about 86percent and a selectivity of about 93percent, at a phenyl mercuric acetate conversion of about 92percent.

Patent; The Halcon SD Group, Inc.; US4316046; (1982); (A) English View in Reaxys

66%

6 : EXAMPLE 6 EXAMPLE 6 Following the procedure of Example 1, 5 mmols of triphenyl tin acetate, 15 mmols of phenyl iodoso diacetate and 2.0 mmols of cupric acetate, together with 20 ml. of acetic acid are charged to the reaction vessel.

After 4 hours of reaction at 100° C. phenyl acetate is found to be produced in a yield of about 66percent and a selectivity of about 72percent, at a triphenyl tin acetate conversion of about 92percent.

Patent; The Halcon SD Group, Inc.; US4316046; (1982); (A) English View in Reaxys

61%

50 : Example 50 Example 50 The reaction was effected in the same manner as Example 44 except for using toluene instead of adamantane.

The conversion of toluene was 67percent, and phenyl acetate (yield 61percent) were formed.

Patent; Daicel Chemical Industries, Ltd.; Ishii, Yasutaka; EP897747; (1999); (A1) English View in Reaxys

58%

5 : EXAMPLE 5 EXAMPLE 5 The procedure of Example 1 is repeated except that 5 mmols of triphenyl tin acetate are employed instead of the phenyl mercuric acetate of Example 1, and 30 mmols of peracetic acid is used.

After 4 hours of reaction at 75° C. there is obtained phenyl acetate in a yield of about 58percent, and in a selectivity of about 68percent, at a triphenyl tin acetate conversion of about 85percent.

Patent; The Halcon SD Group, Inc.; US4316045; (1982); (A) English View in Reaxys

8%

7 : EXAMPLE 7 FOR COMPARISON In a first run, the charge to the reaction vessel consists of 5 mmols phenyl mercuric acetate, 5 mmols phenyl iodoso diacetate and 2.0 mmols sodium acetate, together with 20 ml. of acetic acid.

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After 4 hours of reaction at 75° C. phenyl acetate is produced in a yield of only 8percent and in a 22percent selectivity, at a phenyl mercuric acetate conversion of only 36percent.

Patent; The Halcon SD Group, Inc.; US4316046; (1982); (A) English View in Reaxys Exner,O.; Collection of Czechoslovak Chemical Communications; vol. 26; (1961); p. 1 - 12 View in Reaxys Taylor,E.C. et al.; Journal of the American Chemical Society; vol. 90; (1968); p. 2422 - 2423 View in Reaxys Bruice,T.C. et al.; Journal of the American Chemical Society; vol. 92; (1970); p. 1370 - 1378 View in Reaxys Smissman,E.E. et al.; Journal of Organic Chemistry; vol. 33; (1968); p. 4231 - 4236 View in Reaxys Ansell,M.F. et al.; Journal of the Chemical Society [Section] C: Organic; (1968); p. 217 - 225 View in Reaxys Covello et al.; Annali di Chimica (Rome, Italy); vol. 50; (1960); p. 1651,1662, 1663 View in Reaxys Hewertson et al.; Journal of the Chemical Society; (1962); p. 3267 View in Reaxys Patent; N. Boseki Co.; DE2246334; (1973); ; vol. 78; nb. 160109 View in Reaxys Werber; Shalitin; Bioorganic Chemistry; vol. 2; (1973); p. 202,209 View in Reaxys Oahenfull; Journal of the Chemical Society [Section] B: Physical Organic; (1970); p. 197 View in Reaxys Tanimoto et. al.; Tetrahedron Letters; (1977); p. 2899 View in Reaxys Dorofeenko; J. Gen. Chem. USSR (Engl. Transl.); vol. 31; (1961); p. 994,918; ; nb. 24518; (1961) View in Reaxys Patent; Asahi Chem. Ind.; JP6900055; (1966); ; vol. 70; nb. 114853f; (1969) View in Reaxys Patent; Mc Killop; Taylor; DE1903598; (1969); ; vol. 71; nb. 112025 View in Reaxys Minato et al.; Chemistry Letters; (1977); p. 413,414 View in Reaxys Kanaoka et al.; Chemistry and Industry (London, United Kingdom); (1964); p. 2102 View in Reaxys Kanaoka et al.; Chemical and Pharmaceutical Bulletin; vol. 15; (1967); p. 593,594 View in Reaxys Jacobson et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 6938,6943 View in Reaxys Yamazaki; Higashi; Tetrahedron Letters; (1972); p. 415,416 View in Reaxys Anders; Synthesis; (1978); p. 586 View in Reaxys Weissman; Brown; Journal of Organic Chemistry; vol. 31; (1966); p. 283,286 View in Reaxys White; Emmons; Tetrahedron; vol. 17; (1962); p. 31,32,34 View in Reaxys Sil'berman; Kulikowa; J. Appl. Chem. USSR (Engl. Transl.); vol. 35; (1962); p. 869,838; ; vol. 57; nb. 5848; (1962) View in Reaxys Bonner; Gabb; Journal of the Chemical Society; (1963); p. 3291,3292 View in Reaxys Yamazaki et al.; Synthesis; (1974); p. 436 View in Reaxys Pocker; Beug; Biochemistry; vol. 11; (1972); p. 698,699 - 701 View in Reaxys Starkov et al.; Trudy Tsentral'nogo Nauchno-Issledovatel'skogo Dezinfektsionnogo Instituta; (1962); p. 86,87-90; ; vol. 60; nb.

15768; (1964) View in Reaxys Pachkovskaya et al.; Kinetics and Catalysis; vol. 18; (1977); p. 854

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View in Reaxys Matsui et al.; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 562,565 View in Reaxys Shawali; Biechler; Journal of the American Chemical Society; vol. 89; (1967); p. 3020,3021,3023 View in Reaxys Patent; Sumitomo Chem. Co.; DE2140854; (1970); ; vol. 76; nb. 112894v; (1972) View in Reaxys Yabuuchi; Yakugaku Zasshi; vol. 80; (1960); p. 554; ; vol. 54; nb. 19558; (1960) View in Reaxys Eryshev et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 50; (1977); p. 706,679 View in Reaxys Patent; Asakhi kasei koge kabusiki kaisya; JP55; (1969); Ref. Zh., Khim.; vol. 1; nb. N240P; (1970) View in Reaxys Patent; Chem. Werke witten; NL6406196; (1963); ; vol. 63; nb. 2932cd; (1965) View in Reaxys Patent; Taylor; Mc Killop; US3780021; (1973); ; vol. 85; nb. 32429 View in Reaxys Patent; Farbenfabriken Bayer; DE1288094; (1963); ; vol. 70; nb. 77610b; (1969) View in Reaxys Kubota et al.; Bulletin of the Chemical Society of Japan; vol. 52; (1979); p. 146,148 View in Reaxys Card; Neckers; Inorganic Chemistry; vol. 17; (1978); p. 2345,2347,2349 View in Reaxys Laurence et al.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 33; (1977); p. 353 View in Reaxys Kogan et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 42; (1972); p. 2264,2261,2262-2265 View in Reaxys Jaworski; Kwiatkowski; Roczniki Chemii; vol. 48; (1974); p. 263,268 View in Reaxys Effenberger; Klenk; Chemische Berichte; vol. 107; (1974); p. 175,177,180 View in Reaxys Akhametzhanov et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 46; (1976); p. 578,575 View in Reaxys Henry; Journal of Organic Chemistry; vol. 36; (1971); p. 1886,1888 View in Reaxys Underwood; Bowie; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1977); p. 1670,1672, 1674 View in Reaxys Khoo; Lee; Tetrahedron; vol. 26; (1970); p. 4261,4265, 4266, 4277 View in Reaxys Akahori; Chemical and Pharmaceutical Bulletin; vol. 13; (1965); p. 368,369 View in Reaxys Kaletschitz et al.; Izvestiya Sibirskogo Otdeleniya Akademii Nauk SSSR; vol. 1; (1961); p. 44,48,50; ; vol. 55; nb. 18658 View in Reaxys Takamizawa et al.; Bulletin of the Chemical Society of Japan; vol. 36; (1963); p. 1214,1219 View in Reaxys Williams; Naylor; Journal of the Chemical Society [Section] B: Physical Organic; (1971); p. 1967,1968,1970 View in Reaxys Matsuda et al.; Kogyo Kagaku Zasshi; vol. 70; (1967); p. 1747,1748 View in Reaxys Niwa; Miyake; Chemische Berichte; vol. 102; (1969); p. 1443 View in Reaxys 2 : EXAMPLES 3-6 STR13 EXAMPLES 3-6 STR13 The n-propionate, n-valerate, n-phenylacetate and benzoate derivatives of Virginiamycin M1 were prepared using the respective carbonyl chlorides.

The respective carbonyl chloride (1.0 mmole) was added to a stirring solution of virginiamycin M1 (0.50 g, 0.95 mmole), pyridine (84 μl) and 4-dimethylaminopyridine (20 μg) at room temperature for 2 hours.

Methanol (0.5 ml) was added to destroy excess reagent.

The reaction mixture was partitioned between dichloromethane (3*5 ml) and saturated NaCl (aq) (50 ml).

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The pooled organic layers were dried over anhydrous Na2 SO4 and flash evaporated to dryness (dry weight=0.63, 0.81, 1.0 and 1.4 g respectively).

Purification over a column of 50 g E. Merck silica gel 60 (43-60 μm particle size) in 40-80percent acetone/hexane stepwise gradients yielded 0.43, 0.33, 0.29 and 0.56 g of the respective esters.

R2 =CH2 CH3 (Compound 3) HREI-MS(M+): calculated for C31 H39 N3 O8: 581.2737; found: 581.2737 (300 MHz)H1 -NMR(CD2 Cl2), γ(ppm): 5.77(m), 1.05 (3H, t, J=7.5, CH2 CH3), 2.23 (2H, q, J=7.5, CH2 CH3) (300 MHz)C13 -NMR(CD2 Cl2), γ(ppm): 9.1, 12.4, 12.9, 18.9, 19.7, 27.8, 30.2, 30.5, 38.1, 40.3, 45.2, 45.9, 51.1, 68.0, 81.6, 123.7, 125.5, 126.7, 127.3, 132.9, 136.3, 136.8, 137.1, 143.5, 145.7, 156.3, 160.8, 161.1, 167.2, 173.4, 199.4 FT-IR(ZnSe), v(cm-1): 3345, 2973, 1733, 1673, 1621 Patent; Merck and Co., Inc.; US5242938; (1993); (A) English View in Reaxys Table 3 lists the compounds that I have found to be effective. ...

1,2,6-trihydroxyhexane, 2-hydroxyacetophenone, butyl lactate, phenyl acetate, butyronitrile, methyl ethyl ketoxime, methyl isobutyl ketoxime, ...

Patent; Berg; Lloyd; US5425854; (1995); (A) English View in Reaxys 27.1 : 1.

1.

Formation of phenol acetate 0.5 g of product prepared at example 3E in solution in 10 cm3 of methylene chloride is cooled to +3° C., then 0.5 cm3 of acetic anhydride is added drop by drop, followed by 0.25 cm3 of acetyl chloride, with agitation for 50 minutes.

The reactional medium is diluted with 20 cm3 of iced water, 5 cm3 of an N aqueous solution of sodium hydroxide is added, with agitation for 30 minutes.

After extraction with methylene chloride, the organic phase is washed, dried and the solvents are eliminated under reduced pressure.

0.548 g of crude product is obtained, which is chromatographed on silica (eluent: n-hexane-ethyl acetate, 7-3), and 0.241 g of the expected acetate is recovered.

Patent; Roussel Uclaf; US4900725; (1990); (A) English View in Reaxys 28.1 : 1.

1.

Formation of the phenol acetate A solution comprising 1 g of product obtained at example 21 in 20 cm3 of methylene chloride is cooled to about +5° C., 1 cm3 of acetic anhydride and 0.5 cm3 of acetyl bromide are added, then the temperature is allowed to return to the ambient.

After agitating for 50 minutes, the reactional medium is poured into an iced solution of sodium bicarbonate, agitated for 10 minutes, then extracted with methylene chloride.

The organic phases are separated, washed with water, dried, and the solvents are eliminated under reduced pressure.

The residue is chromatographed on silica (eluent, hexane-ethyl acetate, 80-20, then 85-15).

0.509 g of the acetate (17R) 11-beta-[4-[2-(methylthio)ethoxy]phenyl]-spiro-(estra-1,3,5(10)-trien-17,2'-(5H)-furan)-3-ol is obtained.

Patent; Roussel Uclaf; US4900725; (1990); (A) English View in Reaxys 36.1 : 1.

1.

Formation of the phenol acetate

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The operation is done as in example 28, utilizing at the start 0.250 g of the product obtained in example 20, 0.25 cm3 of acetic anhydride and 0.2 cm3 of acetyl bromide.

After purification by chromatography, 0.150 g of the acetate sought is obtained.

Patent; Roussel Uclaf; US4900725; (1990); (A) English View in Reaxys 2 : EXAMPLE 2 EXAMPLE 2 The procedure of Example 1 is repeated except that 1.0 mmols of cupric acetate is also charged to the flask.

After the 4 hours of reaction at a temperature of 75° C., phenyl acetate yield is found to be about 50percent, based on phenyl mercuric acetate charged, at a phenyl mercuric acetate conversion of about 73percent and a phenyl acetate selectivity of about 68.5percent.

This illustrates the promoting effect of cupric acetate for the reaction.

Patent; The Halcon SD Group, Inc.; US4316046; (1982); (A) English View in Reaxys 3 : EXAMPLE 3 EXAMPLE 3 The procedure of Example 2 is repeated except that 2.0 mmols of cupric acetate are charged to the reaction vessel, and the reaction is carried out for 0.25 hour at 120° C. At the end of this time, phenyl acetate yield is found to be about 48percent, at a phenyl mercuric acetate conversion of about 64percent and a phenyl acetate selectivity of about 75percent.

Patent; The Halcon SD Group, Inc.; US4316046; (1982); (A) English View in Reaxys 11 : EXAMPLE 11 EXAMPLE 11 The general procedure for the conversion of phenols to phenol esters through the intermediate formation of thallous salts is illustrated by the formation of phenyl acetate.

Patent; Taylor; Edward C.; McKillop; Alexander; US3947488; (1976); (A) English View in Reaxys Alicyclic compounds such as: ... p-Methoxybenzoic acid; 4-Methylguaiacol; Methyl phenylacetate; Phenol; Phenyl acetate; Phenylacetic acid; Phenylacetic aldehyde; 2-Phenylethyl acetate; ...

Patent; International Flavors and Fragrances Inc.; US4092333; (1978); (A) English View in Reaxys 27 : Conversion of Acetamide to Phenyl Acetate Using An Alumina-Silica Catalyst at 250° C. EXAMPLE 27 Conversion of Acetamide to Phenyl Acetate Using An Alumina-Silica Catalyst at 250° C. The following reaction was carried out: using the apparatus of Example 16, the pyrolysis tube was charged with 20 ml (16 g) of Harshaw Al 1602 catalyst (91percent Al2 O3, 6percent SiO2), which was calcined for 1 hr at 300° C. under nitrogen.

A reaction solution (17.2 ml) was prepared by dissolving 2 g of acetamide and 6 g of phenol in 10 ml of 1,4-dioxan.

Ten milliliters of this solution were pyrolyzed at 250° C. at a rate of 0.39 ml per min.

The product was 9.29 ml of very pale yellow liquid.

Analysis of the product by the procedure described in Example 1 indicated that 12percent of the acetamide had been converted to phenyl acetate.

Patent; E. I. Du Pont de Nemours and Company; US4161609; (1979); (A) English

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View in Reaxys Aromatic compounds such as: ... p-Methoxybenzoic acid 4-Methylguaiacol Methyl phenylacetate Phenol Phenyl acetate Phenylacetic acid Phenylacetic aldehyde 2-Phenylethyl acetate ...

Patent; International Flavors and Fragrances Inc.; US4096158; (1978); (A) English View in Reaxys 8.2 : Example 8-2 Example 8-2 Synthesis of methyl 4-(N-2-picolylaminomethyl)phenylacetate (Compound V-1) A commercially available 2-picolylamine (92.9 mg) was dissolved in DMF (2 ml) and potassium carbonate (56.5 mg) was added.

After the addition of the compound obtained in Example 8-1 (100.8 mg), the solution was stirred for 1 hour at room temperature.

After the reaction, the reactionsolution was concentrated and the residue was dissolved in chloroform.

The solution was washed with distilled water and dried over anhydrous sodium sulfate.

After the solvent was removed by distillation under reduced pressure, the residue was purified by silica gel column chromatography (5.5 g, chloroform/methanol = 15/1) to obtain the title compound (73.2 mg) as colorless oil.

MS(FAB,Pos.):m/z=271[M+1]+ 1H-NMR(500MHz,CDCl ):γ=1.85(2H,brs),3.62(2H,s),3.69(3H,s), 3 3.83(2H,s),3.92(2H,s),7.15-7.18(1H,m),7.23-7.27(3H,m),7.30-7.36(3H,m),7.64(1H,td,J=7.6,1.7Hz),8.56(1H,ddd,J=5.1,1.7,1.

0Hz).

Patent; Kureha Chemical Industry Co., Ltd.; EP1273571; (2003); (A1) English View in Reaxys The process of claim 3 wherein the developer comprises at least one organic solvent selected from the group consisting of 2octanone, 2-nonanone, 2-heptanone, ... methyl valerate, methyl pentenoate, methyl crotonate, ethyl crotonate, methyl propionate, ethyl propionate, propyl lactate, butyl lactate, isobutyl lactate, amyl lactate, isoamyl lactate, methyl 2-hydroxyisobutyrate, phenyl acetate, benzyl acetate, methyl phenylacetate, benzyl formate, phenylethyl formate, methyl 3-phenylpropionate, benzyl propionate, ethyl phenylacetate, and 2-phenylethyl acetate.

Patent; SHIN-ETSU CHEMICAL CO., LTD.; Sagehashi, Masayoshi; Hatakeyama, Jun; Hasegawa, Koji; US2014/45123; (2014); (A1) English View in Reaxys O

O

O

Cl O

N

HO

N Cl

Rx-ID: 35150689 View in Reaxys 23/238 Yield 98 %

Conditions & References Synthesis of 3 and 5a–d; General Procedure: General procedure: To a solution of alcohol 2 (1 equiv, 2 mmol) in THF (20 mL),AlCl3 (1 equiv) was added followed by stirring for 1 min. 2-Acyl-4,5-pyridazin-3(2H)-one 1 (1 equiv) was then added and the mixture was stirred at room temperature until the alcohol was consumed. The reaction was quenched by the addition of H2O (20 mL), and the mixture was stirred for 10 min at

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room temperature. After the addition of CH2Cl2 (40mL), the organic layer was separated and dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure, and the resulting residue was applied to the top of an open-bed silica gel column. The column was eluted with CH2Cl2 (for 3a–g, 5a and 5b), MeCN–CH2Cl2(1:5 v/v for 3 h), EtOAc–CH2Cl2 (1:1 v/v for 3i), n-hexane–CH2Cl2–EtOAc (4:2:1 v/v for 3j and 3k), or n-hexane–EtOAc (10:1 v/v for 5c and 5d). Fractions containing the product were combined and evaporated under reduced pressure to give the desired esters. Fractions containing 4,5-dichloropyridazin-3(2H)-one were combined and evaporated under reduced pressure to quantitatively give reusable 4,5-dichloropyridazin-3(2H)-one.

Stage 1: With aluminum (III) chloride in tetrahydrofuran, Time= 0.0166667h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 0.166667h, T= 20 °C , Reagent/catalyst, Solvent Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Yoon, Hyo Jae; Lee, Sang-Gyeong; Yoon, Yong-Jin; Synlett; vol. 25; nb. 13; (2014); p. 1909 - 1915; Art.No: ST-2014-U0361-L View in Reaxys 92 %

General Procedure for the Conversion of N-Acylpyridazin-3(2H)-ones into the Corresponding Ester General procedure: Alcohol(1, 5.31 mmol, 1 equiv.) and 2-acylpyridazin-3(2H)-ones (2,6.37 mmol, 1.2 equiv.) were placed in a culture tube (Pyrexbrand 9825 culture tube with screw cap), sealed, and heatedto 100 °C. The resulting mixture was kept at this temperatureuntil 1 disappeared (as determined by TLC analysis). Aftercooling of the tube, dichloromethane (5-6 mL) was added tothe mixture with stirring until the reaction mixture wasdissolved. After removing 4,5-dichloropyridazin-3(2H)-oneby filtration, the resulting filtrate was evaporated underreduced pressure. The resulting residue was further purifiedby silica gel column chromatography to give the correspondingesters 3. in neat (no solvent), Time= 1h, T= 150 °C , Green chemistry Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Kim, Jeum-Jong; Yoon, Yong-Jin; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3410 - 3414 View in Reaxys

88 %

1 : General procedure for the conversion of 2-acylpyridazin-3(2H)-ones into the corresponding ester General procedure: Alcohol (2 or 5, 5.31 mmol, 1 equiv) and 2-acylpyridazin-3(2H)-ones (1k or 4, 6.37 mmol, 1.2 equiv) were placed in a capped vial without solvent or in the presence of tetrahydrofuran (5 mL, 6f and 6g) at room temperature. The resulting mixture was irradiated in aMWoven (300Woutput,1378 kPa) at 150 C for 5 min, until 1k or 4 was consumed. The reaction was monitored by TLC. After cooling Phenyl acetate (3) of the reaction vial, the product was extracted with dichloromethane (6 mL). The reaction mixture was filtered, and the resultant filtrate was evaporated under reduced pressure. The resulting residue was purified further by silica gel column chromatography to give the corresponding esters 3 and 6. Yield: 253 mg, 88percent.

Colorless oil. IR (KBr, CH2Cl2) 3069, 3042, 2927, 2853, 1765, 1593, 1492, 1370, 1213, 1195, 1010, 924, 891, 813, 748, 691, 664 cm-1. 1H NMR (300 MHz, CDCl3) γ 2.25 (s, 3H), 7.03-7.08 (m, 2H), 7.17-7.22 (m, 1H), 7.31-7.37 (m, 2H).

13C

NMR (75 MHz, CDCl3) γ 21.01, 121.69, 125.85, 129.49, 150.86, 169.39. HRMS (m/z): [M]+ calcd for C8H8O2 136.0524.

Found: 136.0521. in tetrahydrofuran, Time= 0.0833333h, T= 150 °C , p= 10336Torr , Microwave irradiation, Solvent, Temperature, Time Kim, Bo Ram; Sung, Gi Hyeon; Lee, Sang-Gyeong; Yoon, Yong Jin; Tetrahedron; vol. 69; nb. 15; (2013); p. 3234 - 3237 View in Reaxys

O

O N

O

HO

N

Rx-ID: 35150697 View in Reaxys 24/238 Yield 78 %

Conditions & References in neat (no solvent), T= 150 °C , Microwave irradiation Kim, Bo Ram; Sung, Gi Hyeon; Lee, Sang-Gyeong; Yoon, Yong Jin; Tetrahedron; vol. 69; nb. 15; (2013); p. 3234 - 3237 View in Reaxys

77 %

in neat (no solvent), Time= 1h, T= 150 °C

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Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Kim, Jeum-Jong; Yoon, Yong-Jin; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3410 - 3414 View in Reaxys 56 %

Stage 1: With aluminum (III) chloride in tetrahydrofuran, Time= 1h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 1h, Reflux Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Yoon, Hyo Jae; Lee, Sang-Gyeong; Yoon, Yong-Jin; Synlett; vol. 25; nb. 13; (2014); p. 1909 - 1915; Art.No: ST-2014-U0361-L View in Reaxys O O

O

O

HO

N

O

Rx-ID: 35150698 View in Reaxys 25/238 Yield

Conditions & References

78 %

in neat (no solvent), Time= 1h, T= 150 °C Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Kim, Jeum-Jong; Yoon, Yong-Jin; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3410 - 3414 View in Reaxys

67 %

in neat (no solvent), T= 150 °C , Microwave irradiation Kim, Bo Ram; Sung, Gi Hyeon; Lee, Sang-Gyeong; Yoon, Yong Jin; Tetrahedron; vol. 69; nb. 15; (2013); p. 3234 - 3237 View in Reaxys

34 %

Stage 1: With aluminum (III) chloride in tetrahydrofuran, Time= 1h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 1h, Reflux Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Yoon, Hyo Jae; Lee, Sang-Gyeong; Yoon, Yong-Jin; Synlett; vol. 25; nb. 13; (2014); p. 1909 - 1915; Art.No: ST-2014-U0361-L View in Reaxys O O O

S N

O

HO

O O

Rx-ID: 35150699 View in Reaxys 26/238 Yield 87 %

Conditions & References in neat (no solvent), Time= 1h, T= 150 °C Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Kim, Jeum-Jong; Yoon, Yong-Jin; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3410 - 3414 View in Reaxys

82 %

in neat (no solvent), T= 150 °C , Microwave irradiation Kim, Bo Ram; Sung, Gi Hyeon; Lee, Sang-Gyeong; Yoon, Yong Jin; Tetrahedron; vol. 69; nb. 15; (2013); p. 3234 - 3237 View in Reaxys

11 %

Stage 1: With aluminum (III) chloride in tetrahydrofuran, Time= 1h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 1h, Reflux Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Yoon, Hyo Jae; Lee, Sang-Gyeong; Yoon, Yong-Jin; Synlett; vol. 25; nb. 13; (2014); p. 1909 - 1915; Art.No: ST-2014-U0361-L View in Reaxys

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45/102

2018-05-09 18:36:04

HO

O

O

O

O

O

HO

O

Rx-ID: 38370813 View in Reaxys 27/238 Yield

Conditions & References With Mg-Al-calcined hydrotalcite(Mg-Al-CHT), Time= 5h, T= 150 °C , Reagent/catalyst, Temperature Rajamanickam, Manivannan; Arumugam, Pandurangan; Kinetics and Catalysis; vol. 55; nb. 3; (2014); p. 299 - 303; Kinet.

Katal.; vol. 55; nb. 3; (2014); p. 313 - 318,6 View in Reaxys

O

O N

O

HO N

N

Rx-ID: 38526504 View in Reaxys 28/238 Yield

Conditions & References

58 %

Stage 1: With aluminum (III) chloride in tetrahydrofuran, Time= 1h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 1h, Reflux Kim, Bo Ram; Sung, Gi Hyeon; Ryu, Ki Eun; Yoon, Hyo Jae; Lee, Sang-Gyeong; Yoon, Yong-Jin; Synlett; vol. 25; nb. 13; (2014); p. 1909 - 1915; Art.No: ST-2014-U0361-L View in Reaxys

O

O

O

O HS

S

O

O

HO

Rx-ID: 35064677 View in Reaxys 29/238 Yield

Conditions & References With poly(N-vinylimidazole) in neat (no solvent), Time= 0.0833333h, T= 20 °C , Green chemistry Khaligh, Nader Ghaffari; RSC Advances; vol. 3; nb. 1; (2013); p. 99 - 110 View in Reaxys

O

O

O

O

O

HO

O HO

O

Rx-ID: 35064678 View in Reaxys 30/238 Yield

Conditions & References With poly(N-vinylimidazole) in neat (no solvent), Time= 0.0833333h, T= 20 °C , Green chemistry Khaligh, Nader Ghaffari; RSC Advances; vol. 3; nb. 1; (2013); p. 99 - 110 View in Reaxys

O

O

O

O

OH

O

O

Rx-ID: 35296626 View in Reaxys 31/238

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

46/102

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Yield

Conditions & References

71 %Chromat.

With pyridine, dipotassium peroxodisulfate, C40H45N2 (1+)*BF4 (1-), palladium diacetate, Time= 24h, T= 80 °C , Reagent/catalyst, Temperature Gary, J. Brannon; Cook, Amanda K.; Sanford, Melanie S.; ACS Catalysis; vol. 3; nb. 4; (2013); p. 700 - 703 View in Reaxys

HO

O

O

O

O

O

O

O

O

O

O O

O

O

O

Rx-ID: 35380625 View in Reaxys 32/238 Yield

Conditions & References With palladium(N,Nγ-bis(salicylidene)ethylenediamine), Mn(acac)3, tetrabutylammomium bromide, oxygen, sodium methylate, p-benzoquinone in dichloromethane, Time= 3h, T= 99.84 °C , p= 50255 - 51755.2Torr , Autoclave, Molecular sieve, Green chemistry, Reagent/catalyst, Solvent, Pressure Yalfani, Mohammad S.; Lolli, Giulio; Wolf, Aurel; Mleczko, Leslaw; Mueller, Thomas E.; Leitner, Walter; Green Chemistry; vol. 15; nb. 5; (2013); p. 1146 - 1149 View in Reaxys

HO

C

O

O

HO

O

O

O

O

O

O

O O

O

O

O

Rx-ID: 35380626 View in Reaxys 33/238 Yield

Conditions & References With palladium(N,Nγ-bis(salicylidene)ethylenediamine), Mn(acac)3, tetrabutylammomium bromide, oxygen, sodium methylate, p-benzoquinone in dichloromethane, Time= 3h, T= 99.84 °C , p= 50255 - 51755.2Torr , Autoclave, Molecular sieve, Green chemistry, Reagent/catalyst, Solvent, Pressure Yalfani, Mohammad S.; Lolli, Giulio; Wolf, Aurel; Mleczko, Leslaw; Mueller, Thomas E.; Leitner, Walter; Green Chemistry; vol. 15; nb. 5; (2013); p. 1146 - 1149 View in Reaxys

H O

O

OH

O

O O H

HO

O

Rx-ID: 36845422 View in Reaxys 34/238 Yield

Conditions & References

24.7 With Peroxyformic acid, Time= 25h, T= 30 °C %Chromat., Li, Xiao-Hong; Meng, Xiang-Guang; Liu, Ying; Peng, Xiao; Green Chemistry; vol. 15; nb. 12; (2013); p. 3332 - 3336 28.5 %Chromat., View in Reaxys 39.8 %Chromat.

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47/102

2018-05-09 18:36:04

O

HO

O

O

Rx-ID: 36845424 View in Reaxys 35/238 Yield

Conditions & References With formic acid, Perbenzoic acid in water, T= 50 °C , Kinetics Li, Xiao-Hong; Meng, Xiang-Guang; Liu, Ying; Peng, Xiao; Green Chemistry; vol. 15; nb. 12; (2013); p. 3332 - 3336 View in Reaxys

O

O

Si

O

O

O

O

Rx-ID: 2346819 View in Reaxys 36/238 Yield

Conditions & References

85 %

With Sulfate, titanium(IV) oxide, Time= 0.5h, T= 20 °C Jin, Tong-Shou; Li, Yan-Wei; Sun, Guang; Li, Tong-Shuang; Journal of Chemical Research, Synopses; nb. 2; (2003); p. 98 100 View in Reaxys

85 %

With polyvinylpolypyrrolidone-bound boron trifluoride in acetonitrile, Time= 3h, T= 20 °C Mokhtary, Masoud; Qandalee, Mohammad; Najafizadeh, Faranak; Comptes Rendus Chimie; vol. 15; nb. 5; (2012); p. 389 393 View in Reaxys

62 %

With silver perchlorate, titanium tetrachloride in dichloromethane, Ambient temperature Miyashita, Mitsutomo; Shiina, Isamu; Miyoshi, So; Mukaiyama, Teruaki; Bulletin of the Chemical Society of Japan; vol.

66; nb. 5; (1993); p. 1516 - 1527 View in Reaxys

O

O

O

O

O

Br

O

O

Br

O

O

O

O

O

O

O O

O

O O O O

Rx-ID: 33116431 View in Reaxys 37/238 Yield 67 %

Conditions & References With pyridine, 1,3 -dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 1,10-Phenanthroline, NiI2*3.5H2O, sodium iodide, zinc, Time= 17h, T= 20 - 60 °C , chemoselective reaction Everson, Daniel A.; Jones, Brittany A.; Weix, Daniel J.; Journal of the American Chemical Society; vol. 134; nb. 14; (2012); p. 6146 - 6159 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

48/102

2018-05-09 18:36:04

O

O N

O

HO

B–

N+

Rx-ID: 33671310 View in Reaxys 38/238 Yield

Conditions & References

84 %

General procedure for the O-acetylation of alcohols using N-acetyl DBN*BPh4 (3a) General procedure: N-acetyl DBN*BPh4 (3a) (1.3 equiv, 0.65 mmol) was added to a carousel tube and purged with nitrogen. Dry MeCN (2 mL), the appropriate alcohol (1 equiv, 0.5 mmol) and DBN (1) (20 mol percent, 0.1 mmol) were added and the resulting solution heated at 80 °C for 16 h. After being cooled to room temperature, the mixture was filtered and concentrated under reduced pressure. The crude product was suspended in a minimum amount of hot CHCl3 and allowed to cool before filtering off the insoluble salts. The filtrate was washed with NH4Cl(aq) and brine before being dried over MgSO4, filtered, and concentrated under reduced pressure.

With DBN in acetonitrile, Time= 16h, T= 80 °C , Inert atmosphere Taylor, James E.; Williams, Jonathan M.J.; Bull, Steven D.; Tetrahedron Letters; vol. 53; nb. 32; (2012); p. 4074 - 4076 View in Reaxys O

O

O

O O

OH

Rx-ID: 33753231 View in Reaxys 39/238 Yield

Conditions & References

25 %

With dipotassium peroxodisulfate, silver(I) acetate in acetonitrile, Time= 24h, T= 100 °C Seo, Sangwon; Taylor, John B.; Greaney, Michael F.; Chemical Communications; vol. 48; nb. 66; (2012); p. 8270 - 8272 View in Reaxys

O

O

OH

O

O

Rx-ID: 33762358 View in Reaxys 40/238 Yield

Conditions & References

88 %

Stage 1: With boron tribromide in dichloromethane, T= 0 - 20 °C , Inert atmosphere Stage 2: in dichloromethane, T= 0 - 20 °C , Inert atmosphere Balaydin, Halis T.; Journal of Chemical Research; vol. 36; nb. 4; (2012); p. 238 - 240 View in Reaxys

O

O

OH

O

HO

O HO

O

Rx-ID: 34079257 View in Reaxys 41/238 Yield 88 %, 12 %

Conditions & References With poly(4-vinylpyridine) perchlorate in neat (no solvent), Time= 0.5h, T= 20 °C Khaligh, Nader Ghaffari; Journal of Molecular Catalysis A: Chemical; vol. 363-364; (2012); p. 90 - 100 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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O O O

O

I O

O

Rx-ID: 34506554 View in Reaxys 42/238 Yield

Conditions & References With [2,2]bipyridinyl, palladium diacetate, acetic anhydride in acetic acid, Time= 6h, T= 100 °C Wang, Nan; McCormick, Theresa M.; Ko, Soo-Byung; Wang, Suning; European Journal of Inorganic Chemistry; nb. 28; (2012); p. 4463 - 4469 View in Reaxys

O O O

O

I Pd

O

O

Rx-ID: 34506555 View in Reaxys 43/238 Yield

Conditions & References

60 %

With 3,3'-bis[N-phenyl-(2-(2'-pyridyl)indolyl)], palladium diacetate, acetic anhydride in acetic acid, Time= 6h, T= 100 °C , Reflux Wang, Nan; McCormick, Theresa M.; Ko, Soo-Byung; Wang, Suning; European Journal of Inorganic Chemistry; nb. 28; (2012); p. 4463 - 4469 View in Reaxys

O

O

O

O

O

Rx-ID: 30575834 View in Reaxys 44/238 Yield

Conditions & References

80 %

With ruthenium hydroxide trichloride in dichloromethane, Time= 3h, T= 160 °C , Autoclave, Inert atmosphere Khusnutdinov; Shchadneva; Khisamova; Dzhemilev; Russian Journal of Organic Chemistry; vol. 47; nb. 2; (2011); p. 155 160 View in Reaxys

O

O

O

O

O

Rx-ID: 31858161 View in Reaxys 45/238 Yield

Conditions & References

612 %Chro- Stage 1: With pyridine, [bis(acetoxy)iodo]benzene, palladium diacetate in acetic acid, Time= 0.0166667h, T= 20 °C mat.

Stage 2: in acetic acid, Time= 1h, T= 100 °C Emmert, Marion H.; Cook, Amanda K.; Xie, Yushu J.; Sanford, Melanie S.; Angewandte Chemie - International Edition; vol. 50; nb. 40; (2011); p. 9409 - 9412 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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O

O

Sn

Rx-ID: 29745353 View in Reaxys 46/238 Yield

Conditions & References 5 Patent; Asahi Kasei Chemicals Corporation; EP2226328; (2010); (A1) English View in Reaxys 5 Patent; Shinohata, Masaaki; Miyake, Nobuhisa; US2010/292496; (2010); (A1) English View in Reaxys

O

O Sn

O

O

Rx-ID: 29745354 View in Reaxys 47/238 Yield

Conditions & References 10 Patent; Asahi Kasei Chemicals Corporation; EP2226328; (2010); (A1) English View in Reaxys 10 Patent; Shinohata, Masaaki; Miyake, Nobuhisa; US2010/292496; (2010); (A1) English View in Reaxys

O O

O

I

O

O

O

O

O

O

Rx-ID: 29845892 View in Reaxys 48/238 Yield 68.1 %Chromat.

Conditions & References With (C5H2N(C6H5)3C5H3N)2(2+)*2BF4 (1-)=(C5H2N(C6H5)3C5H3N)2(BF4)2, palladium diacetate, acetic acid, Time= 24h, T= 100 °C Emmert, Marion H.; Gary, J. Brannon; Villalobos, Janette M.; Sanford, Melanie S.; Angewandte Chemie - International Edition; vol. 49; nb. 34; (2010); p. 5884 - 5886 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

51/102

2018-05-09 18:36:04

O

O

HO

Rx-ID: 32822971 View in Reaxys 49/238 Yield

Conditions & References

75 %

With dihydrogen peroxide in water, Time= 4h, T= 20 °C , Baeyer-Villiger-type reaction Shokrolahi, Arash; Zali, Abbas; Keshavarz, Mohammad Hossein; Chinese Journal of Catalysis; vol. 31; nb. 11-12; (2010); p. 1427 - 1432 View in Reaxys

O

O

O

O

O

O

O

Rx-ID: 10191982 View in Reaxys 50/238 Yield 89 %

Conditions & References With copper(II) sulfate in dichloromethane, Time= 2.5h, Heating Asadolah, Karim; Heravi, Majid M.; Monatshefte fur Chemie; vol. 138; nb. 9; (2007); p. 867 - 869 View in Reaxys

85 %

With 1,4-diaza-bicyclo[2.2.2]octane, bismuth (III) nitrate pentahydrate, Time= 0.05h, Microwave irradiation Asadolah; Heravi; Hekmatshoar; Russian Journal of Organic Chemistry; vol. 45; nb. 7; (2009); p. 1110 - 1111 View in Reaxys

80 %

With iron(III) sulfate in 1,2-dichloro-ethane, Time= 1.5h, Heating Li, Lingjun; Zhu, Lizhi; Zhang, Xinying; Zhang, Guisheng; Qu, Guirong; Canadian Journal of Chemistry; vol. 83; nb. 8; (2005); p. 1120 - 1123 View in Reaxys

O

O

O

O

O

Rx-ID: 3384363 View in Reaxys 51/238 Yield 7 %, 91 %

Conditions & References With hydrogenchloride in chloroform, Time= 11h, T= 20 °C , Baeyer-Villiger oxidation Ghazanfari, Dadkhoda; Hashemi, Mohammed M.; Shahidi-Zandi, Mehdi; Synthetic Communications; vol. 38; nb. 12; (2008); p. 2037 - 2042 View in Reaxys With methyltrifluoromethyldioxirane, (γ5-C5H4SiMe3)2NbH(O)C=CPh2 in tetrahydrofuran, T= 25 °C Fermin, Maria C.; Bruno, Joseph W.; Tetrahedron Letters; vol. 34; nb. 47; (1993); p. 7545 - 7548 View in Reaxys With (γ5-C5H4SiMe3)2NbH(O)C=CPh2, T= 25 °C Fermin, Maria C.; Bruno, Joseph W.; Tetrahedron Letters; vol. 34; nb. 47; (1993); p. 7545 - 7548 View in Reaxys With γ,γ,γ-trifluorotoluene, 3-chloro-benzenecarboperoxoic acid in chloroform, Time= 3.5h, Ambient temperature

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2018-05-09 18:36:04

Kitazume, Tomoya; Kataoka, Junichi; Journal of Fluorine Chemistry; vol. 80; nb. 2; (1996); p. 157 - 158 View in Reaxys

O

O

O

I

O

O

O

O

HO

Rx-ID: 10450936 View in Reaxys 52/238 Yield

Conditions & References With potassium carbonate in acetonitrile, T= 20 °C Thomas, Joshua D.; Sloan, Kenneth B.; Tetrahedron Letters; vol. 47; nb. 49; (2006); p. 8785 - 8787 View in Reaxys

63 % Spectr., 37 % Spectr.

With potassium carbonate in acetonitrile, T= 20 °C Thomas, Joshua D.; Sloan, Kenneth B.; Synthesis; nb. 2; (2008); p. 272 - 278 View in Reaxys NH 2

O

O

OH

O

N N N

Rx-ID: 10527375 View in Reaxys 53/238 Yield

Conditions & References

32 %, 14 %

With lead(IV) acetate in diethyl ether, Time= 1h Vagin, Sergei I.; Frickenschmidt, Antje; Kammerer, Bernd; Hanack, Michael; Chemistry - A European Journal; vol. 13; nb.

3; (2007); p. 985 - 991 View in Reaxys

O

O–

F

OH

O

O

O S F F

I+

O

Si

Rx-ID: 11080172 View in Reaxys 54/238 Yield

Conditions & References

84 %

With potassium fluoride, 18-crown-6 ether in dichloromethane, Time= 4h, T= 20 °C Xue, Jian; Huang, Xian; Synthetic Communications; vol. 37; nb. 13; (2007); p. 2179 - 2185 View in Reaxys

O

O

O

O

O

O

Si

Rx-ID: 10302279 View in Reaxys 55/238 Yield 65 %

Conditions & References With boron trifluoride diethyl etherate, sodium iodide in acetonitrile, Time= 1.5h, T= 0 °C Brar, Anita; Vankar, Yashwant D.; Tetrahedron Letters; vol. 47; nb. 29; (2006); p. 5207 - 5210 View in Reaxys

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2018-05-09 18:36:04

O

O

O

O

O

O

Rx-ID: 10302291 View in Reaxys 56/238 Yield

Conditions & References

69 %

With boron trifluoride diethyl etherate, sodium iodide in acetonitrile, Time= 1.5h, T= 0 °C Brar, Anita; Vankar, Yashwant D.; Tetrahedron Letters; vol. 47; nb. 29; (2006); p. 5207 - 5210 View in Reaxys

F

I

F

F

–O

O F

F

F

Na +

O

O

F

O

O

F

O

F F F O O

Rx-ID: 10439788 View in Reaxys 57/238 Yield

Conditions & References

6.1 g

in n-heptane, Time= 4h, T= 20 °C , Title compound not separated from byproducts El Kharrat, Salem; Laurent, Philippe; Blancou, Hubert; Journal of Organic Chemistry; vol. 71; nb. 18; (2006); p. 6742 6752 View in Reaxys F

F

F

F –O

O

Na +

F F

F F

F

F

O

I

F

F

F

F

F

F

F

F

F

O

F

F O

O

O

F

F

O

O

Rx-ID: 10439792 View in Reaxys 58/238 Yield

Conditions & References in n-heptane, Time= 4h, T= 20 °C , Title compound not separated from byproducts El Kharrat, Salem; Laurent, Philippe; Blancou, Hubert; Journal of Organic Chemistry; vol. 71; nb. 18; (2006); p. 6742 6752 View in Reaxys F F

F F

–O

Na +

F

F

F

F

F

F

I

O

F F

O F

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54/102

2018-05-09 18:36:04

O

O

O F

F

F

F

F

F

O

F

F

F

F

O

O F F

F

F

F

F

F F

F

F

F

F

Rx-ID: 10439793 View in Reaxys 59/238 Yield

Conditions & References Time= 4h, T= 20 °C , Title compound not separated from byproducts El Kharrat, Salem; Laurent, Philippe; Blancou, Hubert; Journal of Organic Chemistry; vol. 71; nb. 18; (2006); p. 6742 6752 View in Reaxys

O O

O

O

O

O

O

O

O

Bi

OH

O

O

Rx-ID: 10445842 View in Reaxys 60/238 Yield

Conditions & References

68 %

With copper diacetate, dicyclohexylmethylamine in dichloromethane, Time= 3h, T= 20 °C , Product distribution, Further Variations: Reagents Ikegai, Kazuhiro; Fukumoto, Kentarou; Mukaiyama, Teruaki; Chemistry Letters; vol. 35; nb. 6; (2006); p. 612 - 613 View in Reaxys O O

O

S

O

O O O

Rx-ID: 10541104 View in Reaxys 61/238 Yield

Conditions & References

92 %

With dimethylamine borane, potassium carbonate, tricyclohexylphosphine, bis(triphenylphosphine)nickel(II) chloride in N,Ndimethyl-formamide, Time= 14h, T= 20 °C Kogan, Vladimir; Tetrahedron Letters; vol. 47; nb. 43; (2006); p. 7515 - 7518 View in Reaxys O O

O

N

OH

O

O

HO O

O

Rx-ID: 11100957 View in Reaxys 62/238 Yield

Conditions & References With water, cetyltrimethylammonim bromide, triethylamine in hexane, butan-1-ol, T= 25 °C , pH= 10.10, Kinetics, Further Variations: pH-values, Reagents Mirgorodskaya; Valeeva; Kudryavtseva; Vylegzhanina; Zuev; Russian Journal of General Chemistry; vol. 76; nb. 4; (2006); p. 590 - 595 View in Reaxys

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-1

O

F –O

O

O

(v4)

F

B FF

O

O

I+

N+

Rx-ID: 9787900 View in Reaxys 63/238 Yield

Conditions & References With tetrabutylammonium perchlorate in chloroform, T= 60 °C , Kinetics Fujita, Morifumi; Wan, Hyeok Kim; Fujiwara, Koji; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 480 - 488 View in Reaxys With tetrabutylammonium perchlorate in chloroform, T= 60 °C Fujita, Morifumi; Wan, Hyeok Kim; Fujiwara, Koji; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 480 - 488 View in Reaxys

O HO

O

methylenedigallic acid

Rx-ID: 12517467 View in Reaxys 64/238 Yield

Conditions & References Reaction Steps: 2 1: 83 percent / Fe2(SO4)3*xH2O / 1.5 h / 20 °C 2: 80 percent / Fe2(SO4)3*xH2O / 1,2-dichloro-ethane / 1.5 h / Heating With iron(III) sulfate in 1,2-dichloro-ethane Li, Lingjun; Zhu, Lizhi; Zhang, Xinying; Zhang, Guisheng; Qu, Guirong; Canadian Journal of Chemistry; vol. 83; nb. 8; (2005); p. 1120 - 1123 View in Reaxys

O

O

I

O

I

O

Rx-ID: 9645407 View in Reaxys 65/238 Yield

Conditions & References

32 %, 59.5 %

in dichloromethane, T= 10 °C Voronkov; Trukhina; Vlasova; Russian Journal of Organic Chemistry; vol. 40; nb. 4; (2004); p. 467 - 469 View in Reaxys

N

O

H N

H N

O

O

OH

HO

O O

HO

N O

Rx-ID: 9665041 View in Reaxys 66/238 Yield

Conditions & References With sodium hydroxide, sodium nitrite in water, T= 25 °C , pH= 3.7, Kinetics

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2018-05-09 18:36:04

Loeppky, Richard N.; Yu, Hongbin; Journal of Organic Chemistry; vol. 69; nb. 9; (2004); p. 3015 - 3024 View in Reaxys

O

OH

N N

O

HO

O

N

N

O

O N

N O

Rx-ID: 9665045 View in Reaxys 67/238 Yield

Conditions & References With sodium hydroxide, sodium nitrite in water, T= 25 °C , pH= 3.7, Kinetics Loeppky, Richard N.; Yu, Hongbin; Journal of Organic Chemistry; vol. 69; nb. 9; (2004); p. 3015 - 3024 View in Reaxys

O

OH

N

N

O

O

O

N

O

N

N

HO

Rx-ID: 9665055 View in Reaxys 68/238 Yield

Conditions & References With sodium hydroxide, sodium nitrite in water, T= 25 °C , pH= 3.7, Kinetics Loeppky, Richard N.; Yu, Hongbin; Journal of Organic Chemistry; vol. 69; nb. 9; (2004); p. 3015 - 3024 View in Reaxys

O

OH

HO

HO

O

O

O OH

O

O

O O

Rx-ID: 9665077 View in Reaxys 69/238 Yield

Conditions & References With HPA, Product distribution, Further Variations: Catalysts Padro; Apesteguia; Journal of Catalysis; vol. 226; nb. 2; (2004); p. 308 - 320 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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2018-05-09 18:36:04

O

HN

O

N

O

HO

O

O

Rx-ID: 9451117 View in Reaxys 70/238 Yield

Conditions & References

80 %

With triethylamine in N,N-dimethyl-formamide, Time= 5h, T= 70 - 80 °C Mashraqui, Sabir H.; Shivaji, Jadhav L.; Journal of Chemical Research - Part S; nb. 3; (2003); p. 121 - 123 View in Reaxys

O

O

Si

Cl

O

O

Rx-ID: 9471991 View in Reaxys 71/238 Yield

Conditions & References

61 %

With montmorillonite K-10 in chloroform, Time= 18h, T= 20 °C Movassagh, Barahman; Atrak, Kobra; Synthetic Communications; vol. 33; nb. 22; (2003); p. 3907 - 3912 View in Reaxys

O I

O

pdCl(CO2Ph)(Ph3P)2

Rx-ID: 9575323 View in Reaxys 72/238 Yield

Conditions & References

58 % Chromat.

in toluene, Time= 2h, T= 20 - 100 °C Yasuda, Hiroyuki; Maki, Noriko; Choi, Jun-Chul; Sakakura, Toshiyasu; Journal of Organometallic Chemistry; vol. 682; nb.

1-2; (2003); p. 66 - 72 View in Reaxys

O

O

N N

O

O

O

O

HO

O

Rx-ID: 10074225 View in Reaxys 73/238 Yield

Conditions & References in benzene, T= 110 °C , Product distribution, Further Variations: Reaction partners Czardybon, Wojciech; Klys, Arkadiusz; Warkentin, John; Werstiuk, Nick Henry; Canadian Journal of Chemistry; vol. 81; nb. 12; (2003); p. 1438 - 1442 View in Reaxys

O

O

I

O

I

O

Rx-ID: 9338093 View in Reaxys 74/238

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Yield

Conditions & References

71 %

T= 20 °C Voronkov; Trukhina; Vlasova; Russian Journal of Organic Chemistry; vol. 38; nb. 11; (2002); p. 1579 - 1581 View in Reaxys

O

O

OH HO

Rx-ID: 9375341 View in Reaxys 75/238 Yield

Conditions & References

84 %

With tetrachloromethane, bis(acetylacetonate)oxovanadium, Time= 1h, T= 200 °C Khusnutdinov; Shchadneva; Baiguzina; Lavrentieva; Dzhemilev; Russian Chemical Bulletin; vol. 51; nb. 11; (2002); p.

2074 - 2079 View in Reaxys

O

O

I

O

HO

Rx-ID: 9375343 View in Reaxys 76/238 Yield

Conditions & References

50 %

Voronkov; Trukhina; Vlasova; Russian Journal of Organic Chemistry; vol. 38; nb. 11; (2002); p. 1576 - 1578 View in Reaxys

O

O SiH

O

O

O

O

O O

O I

Si

O O

O

Rx-ID: 5052148 View in Reaxys 77/238 Yield

Conditions & References With N-ethyl-N,N-diisopropylamine, tris(dibenzylideneacetone)dipalladium(0) chloroform complex, tris-(o-tolyl)phosphine in 1-methyl-pyrrolidin-2-one, Time= 1h, T= 20 °C , Reduction, silylation

77 %

Murata, Miki; Suzuki, Katsuhiro; Watanabe, Shinji; Masuda, Yuzuru; Journal of Organic Chemistry; vol. 62; nb. 24; (1997); p. 8569 - 8571 View in Reaxys With N-ethyl-N,N-diisopropylamine, johnphos, bis(dibenzylideneacetone)-palladium(0) in 1-methyl-pyrrolidin-2-one, Time= 12h, T= 20 °C

75 %

Manoso; DeShong; Journal of Organic Chemistry; vol. 66; nb. 22; (2001); p. 7449 - 7455 View in Reaxys

O

O

OH

O

Rx-ID: 8889224 View in Reaxys 78/238

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Yield

Conditions & References

89 %

With air, zirconium tetraacetate, cobalt(II) acetate, palladium dichloride in acetylacetone, Time= 6h, T= 105 °C , p= 7500.6Torr , Product distribution, Activation energy, Further Variations: Catalysts, Reagents, Pressures, Temperatures, solvents, ratio Mukhopadhyay, Sudip; Rothenberg, Gadi; Lando, Gilad; Agbaria, Kasim; Kazanci, Murat; Sasson, Yoel; Advanced Synthesis and Catalysis; vol. 343; nb. 5; (2001); p. 455 - 459 View in Reaxys

89 %

With air, zirconium tetraacetate, cobalt(II) acetate, palladium dichloride in acetylacetone, Time= 6h, T= 105 °C , p= 7500.6Torr , Product distribution, Activation energy, Kinetics, Further Variations: Catalysts, Reagents, Pressures, Temperatures, solvents, ratio Mukhopadhyay, Sudip; Rothenberg, Gadi; Lando, Gilad; Agbaria, Kasim; Kazanci, Murat; Sasson, Yoel; Advanced Synthesis and Catalysis; vol. 343; nb. 5; (2001); p. 455 - 459 View in Reaxys O

O

O

SiH

O

O

Br

O

O

O O

Si

O O

O

Rx-ID: 8938391 View in Reaxys 79/238 Yield

Conditions & References With N-ethyl-N,N-diisopropylamine, johnphos, bis(dibenzylideneacetone)-palladium(0) in 1-methyl-pyrrolidin-2-one, Time= 12h, T= 60 °C

30 %

Manoso; DeShong; Journal of Organic Chemistry; vol. 66; nb. 22; (2001); p. 7449 - 7455 View in Reaxys

O

O

O

O

O

O

Rx-ID: 9076079 View in Reaxys 80/238 Yield

Conditions & References

45 %

With FeCl3-Montmorillonite K-10, Time= 36h, T= 70 °C Lakouraj, Mansour; Movassagh, B.; Fasihi, J.; Journal of Chemical Research, Synopses; nb. 9; (2001); p. 378 - 379 View in Reaxys HO

O

O

OH

O

HO

OH O

O

Rx-ID: 8630371 View in Reaxys 81/238 Yield

Conditions & References T= 290 °C , Esterification, Acetylation, Product distribution, Further Variations: reaction time Brown, James S.; Glaeser, Roger; Liotta, Charles L.; Eckert, Charles A.; Chemical Communications; nb. 14; (2000); p.

1295 - 1296

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View in Reaxys

O

O

O

HO

HO

O

O

Rx-ID: 8859810 View in Reaxys 82/238 Yield

Conditions & References With sodium oxide, aluminum oxide, T= 280 °C , Product distribution, Further Variations: different persentage compositions of reactans Jain; Journal of the Indian Chemical Society; vol. 77; nb. 7; (2000); p. 355 - 357 View in Reaxys

O

O

O

O

O

HO

Rx-ID: 11158207 View in Reaxys 83/238 Yield

Conditions & References With sodium tetracarbonyl cobaltate in toluene, Kinetics, Further Variations: Solvents Wack, Harald; Drury III, William J.; Taggi, Andrew E.; Ferraris, Dana; Lectka, Thomas; Organic Letters; vol. 1; nb. 12; (1999); p. 1985 - 1988 View in Reaxys Br

Br O

O

O

O

O

O

Rx-ID: 4833018 View in Reaxys 84/238 Yield

Conditions & References With iodine, zinc in dimethyl sulfoxide, Time= 12h, T= 95 °C Kelebekli, Latif; Demir, Uemit; Kara, Yunus; Journal of Chemical Research - Part S; nb. 11; (1997); p. 402 - 403 View in Reaxys Br

Br O

O O

O

O

O O

O

O O

Rx-ID: 4833019 View in Reaxys 85/238 Yield

Conditions & References With acetic acid, zinc in ethanol, Time= 2h, T= 40 - 50 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Kelebekli, Latif; Demir, Uemit; Kara, Yunus; Journal of Chemical Research - Part S; nb. 11; (1997); p. 402 - 403 View in Reaxys

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-1 F (v4)

F –O

B FF

O Na + O+

O

O

O

O HO

Rx-ID: 5056726 View in Reaxys 86/238 Yield

Conditions & References With water, Time= 30h, pH= 9.3, Heating, Decomposition, Further byproducts given Tolstaya; Bobyleva; Vanchikov; Kovalysheva; Kulikov; Tsariev; Russian Chemical Bulletin; vol. 46; nb. 4; (1997); p. 789 797 View in Reaxys H

H

O

O

O

O H

H

Rx-ID: 5070088 View in Reaxys 87/238 Yield

Conditions & References in Cyclohexane-d12, T= 40.5 °C , Decomposition, Kinetics, Further Variations: Temperatures Noh, Taehee; Gan, Hong; Halfon, Sharon; Hrnjez, Bruce J.; Yang, Nien-Chu C.; Journal of the American Chemical Society; vol. 119; nb. 32; (1997); p. 7470 - 7482 View in Reaxys

H

O

O

O

H

O

H

H

H

H

O O

O

O

H

O H

Rx-ID: 8523124 View in Reaxys 88/238 Yield

Conditions & References

15 %

Stage 1: With n-butyllithium, tetramethylpiperidine in tetrahydrofuran, hexane, Time= 0.5h, dry ice:2-propanol cooling; icewater cooling, Decomposition, deketalization Stage 2: in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, hexane, Time= 0.5h, ice-water cooling, Acetylation Noh, Taehee; Gan, Hong; Halfon, Sharon; Hrnjez, Bruce J.; Yang, Nien-Chu C.; Journal of the American Chemical Society; vol. 119; nb. 32; (1997); p. 7470 - 7482 View in Reaxys O

O

O O

N

HO O

O

N

OH

O

O

Rx-ID: 3000188 View in Reaxys 89/238 Yield

Conditions & References With Tris buffer in water, T= 25 °C , Rate constant Colthurst, Matthew J.; Nanni, Matilde; Williams, Andrew; Journal of the Chemical Society. Perkin Transactions 2; vol. 0; nb. 11; (1996); p. 2285 - 2291; Art.No: 6/03575B

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View in Reaxys in water, acetonitrile, T= 25 °C , pH 10.00, Rate constant, Mechanism Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 109; nb. 21; (1987); p.

6362 - 6368 View in Reaxys 2H

O

O O

O

Rx-ID: 4787930 View in Reaxys 90/238 Yield

Conditions & References With deuterium, lt;Ir(cod)(dppe)gt;BF4 in dichloromethane, Ambient temperature Shu; Chen; Heys; Journal of Organometallic Chemistry; vol. 524; nb. 1-2; (1996); p. 87 - 93 View in Reaxys

O C

O

O

<Pd(Me)(OPh)(bpy)>

Rx-ID: 5958489 View in Reaxys 91/238 Yield

Conditions & References

71 % Spectr.

in acetone, Time= 0.5h, p= 760Torr , Ambient temperature Kapteijn, Gerardus M.; Dervisi, Athanasia; Verhoef, Michel J.; Van Den Broek, M.A. Frederik H.; Grove, David M.; Van Koten, Gerard; Journal of Organometallic Chemistry; vol. 517; nb. 1-2; (1996); p. 123 - 131 View in Reaxys

O C

O

O

<Pd(Me)(OPh)(tmeda)>

Rx-ID: 5958490 View in Reaxys 92/238 Yield

Conditions & References

70 % Spectr.

in acetone, Time= 0.5h, p= 760Torr , Ambient temperature Kapteijn, Gerardus M.; Dervisi, Athanasia; Verhoef, Michel J.; Van Den Broek, M.A. Frederik H.; Grove, David M.; Van Koten, Gerard; Journal of Organometallic Chemistry; vol. 517; nb. 1-2; (1996); p. 123 - 131 View in Reaxys H N

C

O

<Pd(Me)-(OPh)(tmeda)>

O

O

N

O

Rx-ID: 7063416 View in Reaxys 93/238 Yield 19 % Chromat., 25 % Chromat.

Conditions & References in acetone, Time= 0.5h, p= 760Torr , Ambient temperature

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Kapteijn, Gerardus M.; Dervisi, Athanasia; Verhoef, Michel J.; Van Den Broek, M.A. Frederik H.; Grove, David M.; Van Koten, Gerard; Journal of Organometallic Chemistry; vol. 517; nb. 1-2; (1996); p. 123 - 131 View in Reaxys

O

O H

O

O

O

O

O

O

H O

O

Rx-ID: 4278704 View in Reaxys 94/238 Yield

Conditions & References T= 500 °C , p= 0.1Torr , flash vacuum thermolysis, Title compound not separated from byproducts Mgani, Quintino A.; Klunder, Antonius J. H.; Nkunya, Mayunga H. H.; Zwanenburg, Binne; Tetrahedron Letters; vol. 36; nb. 26; (1995); p. 4661 - 4664 View in Reaxys

O

O

OH

O

O

O O

Rx-ID: 4354379 View in Reaxys 95/238 Yield

Conditions & References With HZSM-5 zeolite, Time= 48h, T= 119.9 °C , Yield given. Yields of byproduct given Wang, Q. L.; Ma, Yudao; Ji, Xingdong; Yan, Hao; Qiu, Qin; Journal of the Chemical Society, Chemical Communications; nb. 22; (1995); p. 2307 - 2308 View in Reaxys With HZSM-5 zeolite, Time= 48h, T= 149.9 °C , Yield given. Yields of byproduct given Wang, Q. L.; Ma, Yudao; Ji, Xingdong; Yan, Hao; Qiu, Qin; Journal of the Chemical Society, Chemical Communications; nb. 22; (1995); p. 2307 - 2308 View in Reaxys

O

O

OH

O

O

O

O

O O

Rx-ID: 4354380 View in Reaxys 96/238 Yield

Conditions & References With HZSM-5 zeolite, Time= 48h, T= 119.9 °C , var. temp., Product distribution Wang, Q. L.; Ma, Yudao; Ji, Xingdong; Yan, Hao; Qiu, Qin; Journal of the Chemical Society, Chemical Communications; nb. 22; (1995); p. 2307 - 2308 View in Reaxys

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O O

O

O–

N O

O

O

O –O

N O

Rx-ID: 2024558 View in Reaxys 97/238 Yield

Conditions & References in water, T= 25 °C , ionic strength - 0.1 M KCl, Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys With potassium chloride in water, T= 25 °C , Rate constant Stefanidis, Dimitrios; Cho, Sayeon; Dhe-Paganon, Sirano; Jencks, William P.; Journal of the American Chemical Society; vol. 115; nb. 5; (1993); p. 1650 - 1656 View in Reaxys

O

O

N

O

O

N

O

O –O

O

O N

O

O–

N

O O

O

Rx-ID: 2127708 View in Reaxys 98/238 Yield

Conditions & References in water, T= 25 °C , ionic strength - 0.1 M kCl, Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys With potassium chloride in water, T= 25 °C , Rate constant Stefanidis, Dimitrios; Cho, Sayeon; Dhe-Paganon, Sirano; Jencks, William P.; Journal of the American Chemical Society; vol. 115; nb. 5; (1993); p. 1650 - 1656 View in Reaxys

O

O

O HO

O

O

O

O

O

O

O

O

O

Rx-ID: 2391450 View in Reaxys 99/238 Yield 11 % Chromat., 62 % Chromat.

Conditions & References With CeNaY, Time= 4h, T= 210 °C , other substituted phenols, other catalysts, var. temp. and time, Product distribution Rao, Y. V. Subba; Kulkarni, S. J.; Subrahmanyam, M.; Rao, A. V. Rama; Journal of the Chemical Society, Chemical Communications; nb. 18; (1993); p. 1456 - 1457 View in Reaxys

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O

O

O

O

O

N

–O

O–

N

O

O O

Rx-ID: 3000067 View in Reaxys 100/238 Yield

Conditions & References With phenol buffer, potassium chloride, T= 25 °C , γ-deuterium isotope effect, pH 9.05, Rate constant, Mechanism Kovach, Ildiko M.; Elrod, James P.; Schowen, Richard L.; Journal of the American Chemical Society; vol. 102; nb. 25; (1980); p. 7530 - 7534 View in Reaxys With potassium chloride in water, T= 25 °C , Rate constant Stefanidis, Dimitrios; Cho, Sayeon; Dhe-Paganon, Sirano; Jencks, William P.; Journal of the American Chemical Society; vol. 115; nb. 5; (1993); p. 1650 - 1656 View in Reaxys in ethanol, T= 22 °C , Rate constant Guanti, Giuseppe; Cevasco, Giorgio; Thea, Sergio; Dell'Erba, Carlo; Petrillo, Giovanni; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1981); p. 327 - 330 View in Reaxys O

O

O

O

O

N

HO O

O–

N

O O

Rx-ID: 3000189 View in Reaxys 101/238 Yield

Conditions & References With borate buffer, azoniacyclophane CP66 in 1,4-dioxane, T= 25 °C , other pH value, Rate constant Schneider, Hans-Joerg; Kramer, Ruediger; Rammo, Joerg; Journal of the American Chemical Society; vol. 115; nb. 20; (1993); p. 8980 - 8984 View in Reaxys O

O N

O–

O N

O

O

O

HO

O N O

O

N O

O

O

Rx-ID: 3925368 View in Reaxys 102/238 Yield

Conditions & References With borate buffer, azoniacyclophane CP66 in 1,4-dioxane, T= 25 °C , Rate constant Schneider, Hans-Joerg; Kramer, Ruediger; Rammo, Joerg; Journal of the American Chemical Society; vol. 115; nb. 20; (1993); p. 8980 - 8984 View in Reaxys HO

O

O

O

Rx-ID: 18738915 View in Reaxys 103/238

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Yield

Conditions & References Reaction Steps: 2 1: CeNaY / 350 °C 2: 90 percent Chromat. / LaNaY / 350 °C With CeNaY, LaNaY Rao, Y. V. Subba; Kulkarni, S. J.; Subrahmanyam, M.; Rao, A. V. Rama; Journal of the Chemical Society, Chemical Communications; nb. 18; (1993); p. 1456 - 1457 View in Reaxys -1

O

F

O

(v4)

F

Si

B FF

O B

Si

O

O

O

F

O

O

O

N+ N O

Rx-ID: 1938556 View in Reaxys 104/238 Yield

Conditions & References

76 %, 66 %

in 1,1,2-Trichloro-1,2,2-trifluoroethane, 1.) 0 to 55 deg C very slowly, 2.) sonication, reflux, 16 h Olah; Wu; Synthesis; nb. 3; (1991); p. 204 - 206 View in Reaxys

–O

O

O

O

4

O

Pb4+ HO

Rx-ID: 3551799 View in Reaxys 105/238 Yield

Conditions & References With ruthenium trichloride in acetic acid, T= 29.9 °C , variation of ionic strength and dielectric constant of the reaction medium; E(a), log A, ΔH(excit.), ΔS(excit.), ΔG(excit.), Rate constant, Mechanism, Thermodynamic data Pardhasaradhi; Gowda; Journal of the Indian Chemical Society; vol. 68; nb. 6; (1991); p. 327 - 330 View in Reaxys

O

O O

O

O

N

HO O O

N O

Rx-ID: 3869132 View in Reaxys 106/238 Yield

Conditions & References in 1,4-dioxane, water, T= 25 °C , Anion, pH 9.45, Rate constant, Mechanism Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys Cl O

O

O

O HO

Rx-ID: 3924887 View in Reaxys 107/238 Yield

Conditions & References in water, T= 25 °C , Anion, pH 8.98, Rate constant

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Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys

O

O

O

Cl

O

HO

Rx-ID: 3924955 View in Reaxys 108/238 Yield

Conditions & References in methanol, water, T= 25 °C , Anion, pH 8.94, Rate constant Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys

O

O

O

O

O HO

Rx-ID: 3925000 View in Reaxys 109/238 Yield

Conditions & References in methanol, water, T= 25 °C , Anion, pH 8.92, Rate constant Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys N

O

O

O

O

HO

Rx-ID: 3925101 View in Reaxys 110/238 Yield

Conditions & References in methanol, water, T= 25 °C , Anion, pH 8.97, Rate constant Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys

O

O

O

N HO

O

Rx-ID: 3925137 View in Reaxys 111/238 Yield

Conditions & References in methanol, water, T= 25 °C , Anion, pH 8.99, Rate constant Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys

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Cl O

O

HO

O N

O

O

O

Rx-ID: 3925168 View in Reaxys 112/238 Yield

Conditions & References in water, T= 25 °C , Anion, pH 8.98, Rate constant Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys Cl O

O

O

HO

O Cl

Rx-ID: 3925208 View in Reaxys 113/238 Yield

Conditions & References in water, T= 25 °C , Anion, pH 9.01, Rate constant Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys Cl

O

O O

HO

N

O

O

O

Rx-ID: 3925352 View in Reaxys 114/238 Yield

Conditions & References in water, T= 25 °C , Anion, pH 9.01; or 5percent MeOH-water, Rate constant Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys

O

O

HO

O

O

Cl Cl

Rx-ID: 3925824 View in Reaxys 115/238 Yield

Conditions & References in water, T= 25 °C , Anion, pH 8.99; or 5percent MeOH-water, Rate constant Ba-Saif, Salem A.; Colthurst, Matthew; Waring, Mark A.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1991); p. 1901 - 1908 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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(v3)O O O (v8) Pb O O O O O (v3)

O

(v3)

–O

O

2

HO

O

O Pb2+ (v0)

(v3)

Rx-ID: 26718581 View in Reaxys 116/238 Yield

Conditions & References With ruthenium(III)chloride in acetic acid, Kinetics, byproducts: CO2, CH3COOH; at 303 K; TLC Pardhasaradhi; Gowda; Journal of the Indian Chemical Society; vol. 68; nb. 6; (1991); p. 327 - 330 ; (from Gmelin) View in Reaxys

O

O

H 18O

Rx-ID: 3918752 View in Reaxys 117/238 Yield

Conditions & References With carbon monoxide, acetic acid, oxygen-18, palladium diacetate, 1,10-Phenanthroline, Time= 3h, T= 180 °C , p= 22800Torr , Yields of byproduct given Jintoku; Takaki; Fujiwara; Fuchita; Hiraki; Bulletin of the Chemical Society of Japan; vol. 63; nb. 2; (1990); p. 438 - 441 View in Reaxys

O

O HO

Rx-ID: 3918753 View in Reaxys 118/238 Yield

Conditions & References

5.6 %

With carbon monoxide, oxygen, acetic acid, palladium diacetate, 1,10-Phenanthroline, Time= 3h, T= 180 °C , p= 22800Torr , O2 and CO repeatedly supplied every 1 h, Yields of byproduct given Jintoku; Takaki; Fujiwara; Fuchita; Hiraki; Bulletin of the Chemical Society of Japan; vol. 63; nb. 2; (1990); p. 438 - 441 View in Reaxys With oxygen, palladium diacetate, 1,10-Phenanthroline, Time= 1h, T= 180 °C , p= 15Torr , also with 18O2, Mechanism Jintoku; Takaki; Fujiwara; Fuchita; Hiraki; Bulletin of the Chemical Society of Japan; vol. 63; nb. 2; (1990); p. 438 - 441 View in Reaxys

O C

O

O

trans-PdMe(OPh)(PMe3)2

Rx-ID: 5958496 View in Reaxys 119/238 Yield 16 % Chromat.

Conditions & References in dichloromethane, Time= 3h Kim, Yong-Joo; Osakada, Kohtaro; Takenaka, Akio; Yamamoto, Akio; Journal of the American Chemical Society; vol. 112; nb. 3; (1990); p. 1096 - 1104 View in Reaxys

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70/102

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O C

O

O HO

trans-PdMe(OPh)(HOPh)(PMe3)2

Rx-ID: 6208414 View in Reaxys 120/238 Yield

Conditions & References

31 % Chromat.

in dichloromethane, Time= 3h, Ambient temperature Kim, Yong-Joo; Osakada, Kohtaro; Takenaka, Akio; Yamamoto, Akio; Journal of the American Chemical Society; vol. 112; nb. 3; (1990); p. 1096 - 1104 View in Reaxys

O

O

O

N

O

N

N

N

Rx-ID: 1521442 View in Reaxys 121/238 Yield

Conditions & References With sodium hydroxide in acetonitrile, T= 27 °C , Equilibrium constant Gagliano, Ronald A.; Knowlton, Robert C.; Byers, Larry D.; Journal of Organic Chemistry; vol. 54; nb. 22; (1989); p. 5247 5250 View in Reaxys

O

O

O –O

O

O–

O O

Rx-ID: 1627726 View in Reaxys 122/238 Yield

Conditions & References in water, T= 25 °C , ionic strength - 0.1 M KCl, Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys

O–

O

O

O –O

O

N

O O

N O

O

Rx-ID: 2073241 View in Reaxys 123/238 Yield

Conditions & References in water, T= 25 °C , Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys

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71/102

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O

O

O

O –O

O

O

O–

Rx-ID: 2088391 View in Reaxys 124/238 Yield

Conditions & References in water, T= 25 °C , Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys

O N

O

O

O

O

O

N

N

O

O

O

O

–O

N O

O–

O

Rx-ID: 2121704 View in Reaxys 125/238 Yield

Conditions & References in water, T= 25 °C , ionic strength - 0.1 M KCl, Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys

Cl

–O

O –O

O

O

O

N

N O

O

Cl

O

O

Rx-ID: 2144223 View in Reaxys 126/238 Yield

Conditions & References in water, T= 25 °C , ionic strength - 0.1 M KCl, Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys

O O

N

O

O

O–

N

O

–O

O

Cl

O

O

Cl

Rx-ID: 2151069 View in Reaxys 127/238 Yield

Conditions & References in water, T= 25 °C , ionic strength - 0.1 M KCl, Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys

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O O–

N

O

O O

O O

O

O

–O

N

N

N O

O

O O

Rx-ID: 2151681 View in Reaxys 128/238 Yield

Conditions & References in water, T= 25 °C , ionic strength - 0.1 M KCl, Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys Cl Cl

O

O

O

O

O

–O

N

O–

N

O

O O

Rx-ID: 2206368 View in Reaxys 129/238 Yield

Conditions & References in water, T= 25 °C , ionic strength 0.1 M KCl, Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys O

O O

O

N

O N

O

O

–O

O–

O N

O

O

O

N O

Cl Cl

Rx-ID: 2261625 View in Reaxys 130/238 Yield

Conditions & References in water, T= 25 °C , ionic strength - 0.1 M KCl, Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys

O

O

O

O

N

N

N

N

Rx-ID: 3701509 View in Reaxys 131/238 Yield

Conditions & References With sodium hydroxide in acetonitrile, T= 27 °C , Equilibrium constant Gagliano, Ronald A.; Knowlton, Robert C.; Byers, Larry D.; Journal of Organic Chemistry; vol. 54; nb. 22; (1989); p. 5247 5250 View in Reaxys

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O

–O

O O

O

–O

O

O O

O

N

O N

N

O

O

N O

Rx-ID: 3869126 View in Reaxys 132/238 Yield

Conditions & References With phenol buffer, potassium chloride, T= 25 °C , γ-deuterium isotope effect, pH 9.05, Rate constant, Mechanism Kovach, Ildiko M.; Elrod, James P.; Schowen, Richard L.; Journal of the American Chemical Society; vol. 102; nb. 25; (1980); p. 7530 - 7534 View in Reaxys in water, T= 25 °C , ionic strength - 0.1 M KCl, Rate constant Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p.

2647 - 2652 View in Reaxys

O C

HO

O

O

Fe2(CO)8CH2

Rx-ID: 5958493 View in Reaxys 133/238 Yield

Conditions & References

30 %

in hexane, T= 70 °C , p= 30400Torr Denise, B.; Navarre, D.; Rudler, H.; Daran, J. C.; Journal of Organometallic Chemistry; vol. 375; (1989); p. 273 - 289 View in Reaxys

OH

HO

O

N

O

I

O

O

Rx-ID: 25188671 View in Reaxys 134/238 Yield

Conditions & References

90%

8 : DMAE And TMAE Phenylacetate TMAE phenylacetate was prepared by adding 0.013 moles of methyl iodide to 0.010 moles of DMAE phenylacetate in 50 ml of acetone and allowing the reaction to proceed overnight at room temperature.

The white crystalline material was filtered, washed twice with 50 ml of ethyl ether and dried.

The yield was 90percent. in acetone Patent; Abood; Leo G.; US4835162; (1989); (A) English View in Reaxys

O

Cl

O

N O

OH

Rx-ID: 25197726 View in Reaxys 135/238 Yield

Conditions & References 8 : DMAE And TMAE Phenylacetate EXAMPLE 8 DMAE And TMAE Phenylacetate

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To 0.05 moles of dry dimethylaminoethanol in 100 ml of dry methylene chloride at room temperature was added slowly with stirring over a period of 15 min. 0.05 ml of phenylacetyl chloride in 50 ml of methylene chloride.

After another 30 min., the contents were extracted with H2 O and the organic phase concentrated in vacuo.

The final product was purified by distillation at 5mm Hg and 168° C. The yield was 55percent.

An infrared analysis of DMAE phenylacetate yielded the following bands: in dichloromethane Patent; Abood; Leo G.; US4835162; (1989); (A) English View in Reaxys

O

Ir

O

(v4)

P

O

H

(v3)

(v4)

P

P

(v4)

Ir

O

Cl

Cl (v4) (v4)

P

O

(v6)

P

Ir P (v6)

(v4)

(v3)

O

(v4)

Cl

O

(v3)

Cl

Rx-ID: 26632480 View in Reaxys 136/238 Yield

Conditions & References With acetyl chloride in cyclohexane, soln. placed in a pressure tube fitted with a Teflon stopcock, degassed (vac.), acetyl chloride distilled onto the soln., stirred (1 h), solvent removed by vac. distillation Bernard, Karen A.; Atwood, Jim D.; Organometallics; vol. 8; (1989); p. 795 - 800 ; (from Gmelin) View in Reaxys

O

O

O

O

O

–O

Rx-ID: 2350807 View in Reaxys 137/238 Yield

Conditions & References

97 %

With Amberlite IRA-400, Time= 1.5h, Ambient temperature Ram, B.; Roy, J.; Sarkar, A.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol.

27; nb. 1-12; (1988); p. 665 View in Reaxys

O

O O

O

O O O

O

O

O

Rx-ID: 3918751 View in Reaxys 138/238 Yield

Conditions & References With dihydrogen peroxide, acetic anhydride, different molar ratios, Product distribution Monden; Manaka; Kasama; Kotani; Tobinaga; Chemical and pharmaceutical bulletin; vol. 36; nb. 5; (1988); p. 1926 - 1929 View in Reaxys

O

O

O

O

O

HO

Rx-ID: 3924487 View in Reaxys 139/238

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Yield

Conditions & References

100 %

With potassium carbonate, Aliquat 336 in neat (no solvent), Time= 0.5h, T= 70 °C Barry, Jean; Bram, Georges; Petit, Alain; Tetrahedron Letters; vol. 29; nb. 36; (1988); p. 4567 - 4568 View in Reaxys

100 %

With potassium carbonate, Aliquat 336 in neat (no solvent), Time= 0.5h, T= 70 °C , Product distribution Barry, Jean; Bram, Georges; Petit, Alain; Tetrahedron Letters; vol. 29; nb. 36; (1988); p. 4567 - 4568 View in Reaxys O N+ O

O

N+

O

S

S N–

O S

HO O

O

O S N–

O

O

O

N H

N

Rx-ID: 3926256 View in Reaxys 140/238 Yield

Conditions & References

61 %, 96 %

in tetrachloromethane, 1.) 16 h, reflux, 2.) 48 h, 20 deg C Blaschette, Armand; Linoh, Karin; Safari, Firouz; Schiebel, Hans-Martin; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 43; nb. 12; (1988); p. 1639 - 1646 View in Reaxys

O

O

O

Si Si O

O

Rx-ID: 1938541 View in Reaxys 141/238 Yield

Conditions & References With phosphorus pentaoxide, 1) 50 deg C, 1 h, 2) 80 deg C, 4 h, Yield given. Multistep reaction Rao, C. Someswara; Rambabu, M.; Srinivasan, P. S.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 26; nb. 1-12; (1987); p. 407 - 411 View in Reaxys

O

O

HO

O

Rx-ID: 2055818 View in Reaxys 142/238 Yield 61 %

Conditions & References With sodium acetate in acetic anhydride, Time= 30h, Heating Murali, D.; Rao, G. S. Krishna; Synthesis; nb. 3; (1987); p. 254 - 256 View in Reaxys

HO

O

O

O

O

Rx-ID: 2202792 View in Reaxys 143/238 Yield

Conditions & References thermal pyrolysis

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August, Ryan; McEwen, Ian; Taylor, Roger; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 1683 - 1690 View in Reaxys

O

O

O

OH

O HO

HO

Rx-ID: 2885205 View in Reaxys 144/238 Yield

Conditions & References With oxygen, palladium diacetate, carbon monoxide, 1,10-phenanthroline hydrate, Time= 12h, T= 180 °C , Yield given. Yields of byproduct given Jintoku, Tetsuro; Taniguchi, Hiroshi; Fujiwara, Yuzo; Chemistry Letters; (1987); p. 1865 - 1868 View in Reaxys

O

O

O HO

HO

Rx-ID: 3918750 View in Reaxys 145/238 Yield

Conditions & References With palladium diacetate, carbon monoxide, oxygen, 1,10-phenanthroline hydrate, Time= 12h, T= 180 °C , var. catalyst; ratio of reagents, Product distribution Jintoku, Tetsuro; Taniguchi, Hiroshi; Fujiwara, Yuzo; Chemistry Letters; (1987); p. 1865 - 1868 View in Reaxys

O Si O

O

HO

O

Rx-ID: 3924773 View in Reaxys 146/238 Yield

Conditions & References With phosphorus pentaoxide, 1) 50 deg C, 1 h, 2) 70 deg C, 3 h, Yield given. Multistep reaction Rao, C. Someswara; Rambabu, M.; Srinivasan, P. S.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 26; nb. 1-12; (1987); p. 407 - 411 View in Reaxys

O HO

O

phosphorous oxychloride

Rx-ID: 19587090 View in Reaxys 147/238 Yield

Conditions & References Reaction Steps: 2 1: 35 percent 2: thermal pyrolysis August, Ryan; McEwen, Ian; Taylor, Roger; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 1683 - 1690 View in Reaxys

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77/102

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O

O

Rx-ID: 25002817 View in Reaxys 148/238 Yield

Conditions & References 7 : EXAMPLE 7 EXAMPLE 7 The procedure of Example 4 was repeated except that 0.874 mol of acetic acid was used in place of the lauric acid.

The reaction was carried out at about 85° C. for 3 hours.

Analysis showed that only a trace amount of phenyl acetate formed and 8 millimols of biphenyl were formed.

Patent; Goel; Anil B.; Grimm; Robert A.; US4655974; (1987); (A) English View in Reaxys

O

O

O

O O

O

O O

Cl

Rx-ID: 2019071 View in Reaxys 149/238 Yield

Conditions & References

90 % Chromat., 5 % Chromat.

With 1,1'-bipyridyl, triphenylphosphine, nickel dichloride, zinc in N,N-dimethyl acetamide, T= 50 - 80 °C Colon, Ismael; Kelsey, Donald R.; Journal of Organic Chemistry; vol. 51; nb. 14; (1986); p. 2627 - 2637 View in Reaxys

O

O

O

O

O

O

O

O

O

Rx-ID: 3139979 View in Reaxys 150/238 Yield

Conditions & References in diphenylether, T= 135 - 176 °C , Ea, log A, Thermodynamic data Ito, Yoshikatsu; Tone, Mutsuo; Yokoya, Hiroaki; Matsuura, Teruo; Schuster, Gary B.; Journal of Organic Chemistry; vol.

51; nb. 12; (1986); p. 2240 - 2245 View in Reaxys

F F F

F

F

F

F F

F

F

F

F F

O

F

F F

O

F

O

F

F

F

F

F

F

O F

F

F

O OH

Rx-ID: 3917279 View in Reaxys 151/238

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Yield

Conditions & References

3 %, 62 %, 6%

With lead(IV) acetate, Time= 7h, T= 80 °C , Mechanism, Product distribution Serguchev, Yu. A.; Davydova, V. G.; Makhon'kov, D. I.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 1006 - 1011; Zhurnal Organicheskoi Khimii; vol. 22; nb. 6; (1986); p. 1121 - 1126 View in Reaxys

O

O O

O

O O

Cl

Bi

Rx-ID: 2697745 View in Reaxys 152/238 Yield

Conditions & References With copper dichloride in tetrahydrofuran, Time= 30h, T= 20 °C , Yield given. Yields of byproduct given Dodonov, V. A.; Gushin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 11; (1985); p. 2514 2519,2232 - 2236 View in Reaxys

O

O O

O

O O

Bi

Rx-ID: 2697746 View in Reaxys 153/238 Yield

Conditions & References in toluene, Time= 30h, T= 100 °C , Yield given. Yields of byproduct given Dodonov, V. A.; Gushin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 11; (1985); p. 2514 2519,2232 - 2236 View in Reaxys Time= 30h, T= 150 °C , Yield given. Yields of byproduct given Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 1; (1985); p. 73 - 80,63 68 View in Reaxys

O O

O O

Bi

N H

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79/102

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O

O

N

Rx-ID: 2877941 View in Reaxys 154/238 Yield

Conditions & References With copper diacetate in tetrahydrofuran, Time= 100h, T= 18 °C , Yield given. Yields of byproduct given Dodonov, V. A.; Gushin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 11; (1985); p. 2514 2519,2232 - 2236 View in Reaxys

O

O

O

O

O O

O

Rx-ID: 2940833 View in Reaxys 155/238 Yield

Conditions & References

42 %, 2.7 % With peracetic acid, ferrous perchlorate, acetonitrile Kotani, Eiichi; Kobayashi. Shigeki; Ishii, Yoko; Tobinaga, Seisho; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 11; (1985); p. 4671 - 4679 View in Reaxys

O O

H N

O O

Bi

O

O

N

Rx-ID: 2961562 View in Reaxys 156/238 Yield

Conditions & References With copper diacetate in tetrahydrofuran, Time= 74h, T= 50 °C , Yield given. Yields of byproduct given Dodonov, V. A.; Gushin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 11; (1985); p. 2514 2519,2232 - 2236 View in Reaxys

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O

O O

O

O O

Bi

N

N H

Rx-ID: 3303679 View in Reaxys 157/238 Yield

Conditions & References With copper diacetate in tetrahydrofuran, Time= 100h, T= 18 °C , Yield given. Yields of byproduct given Dodonov, V. A.; Gushin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 11; (1985); p. 2514 2519,2232 - 2236 View in Reaxys

O O

H N

O

O

O O

H 2N

Bi

Rx-ID: 3374077 View in Reaxys 158/238 Yield

Conditions & References With copper diacetate in tetrahydrofuran, Time= 100h, T= 18 °C , Yield given. Yields of byproduct given Dodonov, V. A.; Gushin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 11; (1985); p. 2514 2519,2232 - 2236 View in Reaxys

O

O

O

O

OH

O

O

O

O

Rx-ID: 3916900 View in Reaxys 159/238 Yield

Conditions & References

4.6 %, 66.6 %

With ferrous perchlorate, acetonitrile, trifluoroacetic anhydride, Time= 5h, T= 30 °C Kotani, Eiichi; Kobayashi. Shigeki; Ishii, Yoko; Tobinaga, Seisho; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 11; (1985); p. 4671 - 4679 View in Reaxys

O O

H N

O O

Bi

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O

O

Ph2BiOAc

N

Rx-ID: 6218219 View in Reaxys 160/238 Yield

Conditions & References

3 %, 60 %

With copper diacetate in tetrahydrofuran, T= 50 °C Dobonov, V. A.; Gushchkin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 2; (1985); p. 466 467,413 View in Reaxys

(v3)

O N N (v4) 2+ (v4)

N

Ni

(v4) –H C (v4) 3

(v4)

O–

O

Ni

N

(v2)

O

(v4)

O

(v4)

(v3)

Rx-ID: 26989473 View in Reaxys 161/238 Yield

Conditions & References

100 %

With carbon monoxide in tetrahydrofuran, (N2 or Ar), complex dissolved in THF, evacuated, excess CO introduced at room temp.C for 0.3 h; IR Komiya, Sanshiro; Akai, Yasushi; Tanaka, Kohkichi; Yamamoto, Takakazu; Yamamoto, Akio; Organometallics; vol. 4; (1985); p. 1130 - 1136 ; (from Gmelin) View in Reaxys

31 %

With carbon monoxide in tetrahydrofuran, (N2 or Ar), complex dissolved in THF, evacuated, equimolar amount CO introduced at -78°C for 10 h; IR Komiya, Sanshiro; Akai, Yasushi; Tanaka, Kohkichi; Yamamoto, Takakazu; Yamamoto, Akio; Organometallics; vol. 4; (1985); p. 1130 - 1136 ; (from Gmelin) View in Reaxys

O P–

(v4)

Ni 2+

O

P

O

(v4) (v4)

P–

O (v3)

Ni O

P

(v3)

(v4)

Rx-ID: 26990372 View in Reaxys 162/238 Yield

Conditions & References

90 %

With carbon monoxide in diethyl ether, (N2 or Ar), complex dissolved in Et2O, evacuated, excess CO introduced at room temp. for 24 h; IR Komiya, Sanshiro; Akai, Yasushi; Tanaka, Kohkichi; Yamamoto, Takakazu; Yamamoto, Akio; Organometallics; vol. 4; (1985); p. 1130 - 1136 ; (from Gmelin) View in Reaxys

O

Cl

O

OH

O

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O O

O

O

O

O

O

O

Cl

O

O

O

Rx-ID: 2882540 View in Reaxys 163/238 Yield

Conditions & References Time= 24h, T= 120 °C , Yield given. Yields of byproduct given Pusino, A.; Rosnati, V.; Saba, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1893 - 1900 View in Reaxys With lithium acetate, Time= 15h, T= 90 °C , other reagents, Rate constant, Product distribution Pusino, A.; Rosnati, V.; Saba, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1893 - 1900 View in Reaxys

O O

OH

2H

O

Cl O O

O

O

O

O

Cl

O

Rx-ID: 2882577 View in Reaxys 164/238 Yield

Conditions & References With lithium acetate, Time= 15h, T= 100 °C , other reagents, Rate constant, Product distribution Pusino, A.; Rosnati, V.; Saba, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1893 - 1900 View in Reaxys

O

O

P

Rx-ID: 3449542 View in Reaxys 165/238 Yield 60 %, 5 %, 18 %

Conditions & References With palladium diacetate, palladium diacetate in toluene, T= 80 °C , Pd(II) catalyzed cleavage, Mechanism Goel, Anil B.; Richards, H. J.; Kyung, J. H.; Tetrahedron Letters; vol. 25; nb. 4; (1984); p. 391 - 392 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

83/102

2018-05-09 18:36:04

O

N

O

O

O

N

Rx-ID: 20791916 View in Reaxys 166/238 Yield

Conditions & References Reaction Steps: 2 2: LiOAc / 15 h / 90 °C / other reagents With lithium acetate Pusino, A.; Rosnati, V.; Saba, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1893 - 1900 View in Reaxys

F F F

F

F

F

F

F

F

F

F

F

HO F O

F

F

F O OH

F

F

F F F

O

F F

F

O

Cl

O F

F

F

O F

F

Rx-ID: 3755901 View in Reaxys 167/238 Yield

Conditions & References With lead(IV) acetate, lithium chloride, Time= 7h, T= 80 °C , various ratio of reagents studied, Product distribution, Mechanism Serguchev, Yu. A.; Davydova, V. G.; Stetsyuk, G. A.; Blendonogii, D. P.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 19; nb. 4; (1983); p. 726 - 730; Zhurnal Organicheskoi Khimii; vol. 19; nb. 4; (1983); p. 820 824 View in Reaxys

F F F

F

F

F

F

F

–

O

4 F

F

F

F

O Pb4+

F O OH

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

84/102

2018-05-09 18:36:04

F

F

F F F

O

F

O

F

F

O F

F

F

O F

F

Rx-ID: 3917278 View in Reaxys 168/238 Yield

Conditions & References

2.8 %, 62.4 %, 6.4 %

Time= 7h, T= 80 °C Serguchev, Yu. A.; Davydova, V. G.; Stetsyuk, G. A.; Blendonogii, D. P.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 19; nb. 4; (1983); p. 726 - 730; Zhurnal Organicheskoi Khimii; vol. 19; nb. 4; (1983); p. 820 824 View in Reaxys Br O

O

O

O

Rx-ID: 1988282 View in Reaxys 169/238 Yield

Conditions & References With di-tert-butyl peroxide, tri-n-butyl-tin hydride in diethyl ether, Irradiation, Yield given Shahidi, Fereidoon; Tidwell, Thomas T.; Canadian Journal of Chemistry; vol. 60; (1982); p. 1092 - 1097 View in Reaxys O

O

O

O O

O

O

O

HO

O O

O

O

HO

O

OH

Rx-ID: 2155991 View in Reaxys 170/238 Yield

Conditions & References

36 %, 10 %, in benzene, Time= 48h, T= 100 °C 42 %, 12 % Shahidi, Fereidoon; Tidwell, Thomas T.; Canadian Journal of Chemistry; vol. 60; (1982); p. 1092 - 1097 View in Reaxys

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85/102

2018-05-09 18:36:04

O

OH

O O

O P

O

O

O

H

O P

O

O

O

O

O

O

O

O

P

O

O

O

O

Rx-ID: 2883775 View in Reaxys 171/238 Yield

Conditions & References

45 %, 29.2 Time= 3h, T= 100 °C %, 35 %, 33 Gazizov, T. Kh.; Belyalov, R. U.; Pudovik, A. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 3; (1982); p. 487 - 491,428 % - 430 View in Reaxys

O

O

Cl

Cl

Sn

O

O

Rx-ID: 3316441 View in Reaxys 172/238 Yield 45 % Chromat., 73 % Chromat.

Conditions & References With benzylbis(triphenylphosphine)palladium(II) chloride, Time= 48h, T= 63 °C , other reactant and organic partners systems, temp., and time; var. ethers, Mechanism, Product distribution Pri-Bar, I.; Stille, J. K.; Journal of Organic Chemistry; vol. 47; nb. 7; (1982); p. 1215 - 1220 View in Reaxys

O

O

I

Rx-ID: 25118665 View in Reaxys 173/238 Yield 10%

Conditions & References 2 : EXAMPLE 2 EXAMPLE 2 Following the procedure of Example 1, 5 mmols of phenyl mercuric acetate, 5 mmols of peracetic acid and 1.0 mmol of phenyl iodide, together with 20 ml. of acetic acid as solvent, are charged to the reaction vessel.

After 18 hours of reaction at a temperature of 75° C., phenyl acetate yield is found to be formed in a yield of about 10percent, based on the phenyl mercuric acetate charged. in acetic acid Patent; The Halcon SD Group, Inc.; US4316045; (1982); (A) English View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

86/102

2018-05-09 18:36:04

O

O

O

HO

Rx-ID: 850906 View in Reaxys 174/238 Yield

Conditions & References With diethyl ether, sulfuric acid, T= 20 °C Hurd; Roe; Journal of the American Chemical Society; vol. 61; (1939); p. 3355,3357 View in Reaxys With diethyl ether, T= 180 °C Patent; Roehm and Haas Co.; US1898687; (1931) View in Reaxys Rice et al.; Journal of the American Chemical Society; vol. 56; (1934); p. 1760,1765 View in Reaxys With diethyl ether, toluene-4-sulfonic acid, T= 20 °C Hurd; Roe; Journal of the American Chemical Society; vol. 61; (1939); p. 3355,3357 View in Reaxys With diethyl ether, T= 80 °C Spring; Vickerstaff; Journal of the Chemical Society; (1935); p. 1873 View in Reaxys T= 80 °C Spring; Vickerstaff; Journal of the Chemical Society; (1935); p. 1873 View in Reaxys T= 180 °C Patent; Roehm and Haas Co.; US1898687; (1931) View in Reaxys Roehm and Haas Co; Chem. Zentralbl.; vol. 104; nb. I; (1933); p. 3243 View in Reaxys Rice et al.; Journal of the American Chemical Society; vol. 56; (1934); p. 1760,1765 View in Reaxys

1.24 g

With silica gel, Ambient temperature, var. of support/reagent, temp., Product distribution Chihara, Teiji; Teratani, Shousuke; Ogawa, Haruo; Journal of the Chemical Society, Chemical Communications; nb. 21; (1981); p. 1120 View in Reaxys

O

Br

OH

O

O

OH

Rx-ID: 2880020 View in Reaxys 175/238 Yield 50 %

Conditions & References With triethylamine, triphenylphosphine, Time= 4h, T= 200 °C Hashimoto, Shizunobu; Furukawa, Isao; Bulletin of the Chemical Society of Japan; vol. 54; nb. 9; (1981); p. 2839 - 2840 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

87/102

2018-05-09 18:36:04

O

O

O

HO

N

O

Rx-ID: 1638096 View in Reaxys 176/238 Yield

Conditions & References

86 %

in dichloromethane, Time= 12h, T= 20 °C Effenberger, Franz; Bessey, Eberhard; Chemische Berichte; vol. 113; nb. 6; (1980); p. 2100 - 2109 View in Reaxys O

O

O O

O

O

O

Cl Cl

O

Rx-ID: 2021662 View in Reaxys 177/238 Yield

Conditions & References in tetrachloromethane, T= 90 °C , a comparative CIDNP study of the photochemical decomposition, Mechanism, Product distribution Nedelec, J. Y.; Lefort, D.; Tetrahedron; vol. 36; (1980); p. 3199 - 3204 View in Reaxys

O

O

O

O O O

O

Rx-ID: 2184855 View in Reaxys 178/238 Yield 65 %, 74 %

Conditions & References With antimonypentachloride in dichloromethane, Time= 1h, other reagent, Product distribution Miura, Masahiro; Nojima, Masamoto; Kusabayashi, Shigekazu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1950 - 1954 View in Reaxys

65 %, 74 %

With antimonypentachloride in dichloromethane, Time= 1h Miura, Masahiro; Nojima, Masamoto; Kusabayashi, Shigekazu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1950 - 1954 View in Reaxys

O

O

O

S

HO

S O

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

88/102

2018-05-09 18:36:04

O

O

S

O

S O

Rx-ID: 2391446 View in Reaxys 179/238 Yield

Conditions & References

58 %, 13 %

Furukawa, Naomichi; Morishita, Tsuyoshi; Akasaka, Takeshi; Oae, Shigeru; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 432 - 440 View in Reaxys

O

O

Cl

P

O

O

O

P

O O

Cl

O

Rx-ID: 3315619 View in Reaxys 180/238 Yield

Conditions & References With hydrogenchloride, Time= 1.5h, T= 75 °C , Mechanism Gazizov, T. Kh.; Belyalov, R. U.; Pudovik, A. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 50; nb. 8; (1980); p. 1673 1677,1355 - 1359 View in Reaxys

O

O

O

O S O

O

Rx-ID: 3700844 View in Reaxys 181/238 Yield

Conditions & References With 2,2'-azobis(isobutyronitrile), tri-n-butyl-tin hydride in toluene, Heating, Yield given Barton, Derek H. R.; Dowlatshahi, Hussein A.; Motherwell, William B.; Villemin, Didier; Journal of the Chemical Society, Chemical Communications; nb. 15; (1980); p. 732 - 733 View in Reaxys O N

HO N O

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

89/102

2018-05-09 18:36:04

O

O

O

O

unidentified compounds

O

O

Rx-ID: 6732010 View in Reaxys 182/238 Yield

Conditions & References

1.2 %, 38 % With copper diacetate, oxygen, potassium thioacyanate, potassium thioacyanate, copper diacetate in N,N-dimethyl-formamide, Time= 0.5h, T= 49 - 102 °C , p= 25742.8Torr , variable reaction time, different concentrations of catalysts, steel and PTFE-lined reactors, Rate constant, Product distribution Beltrame, Paolo; Beltrame, Pier Luigi; Bussola, Marzio; Carniti, Paolo; Gazzetta Chimica Italiana; vol. 110; nb. 2/3; (1980); p. 141 - 146 View in Reaxys 2 Cl –

O

Cl

O

Fe 2+

O

2 N

N

O–

N

Fe 2+

N

Rx-ID: 26977203 View in Reaxys 183/238 Yield 25 %

Conditions & References in tetrahydrofuran, under N2, Fe complex in THF treated with CH3COCl for 1 d; volatiles removed, identified by IR, elem. anal.

Komiya, Sanshiro; Tane-ichi, Shoshiro; Yamamoto, Akio; Yamamoto, Takakazu; Bulletin of the Chemical Society of Japan; vol. 53; nb. 3; (1980); p. 673 - 679 ; (from Gmelin) View in Reaxys

O

O

OH

O

O B

O

O

Rx-ID: 26352857 View in Reaxys 184/238 Yield 95 %

Conditions & References in neat (no solvent), byproducts: H3BO3; boiling for 1h; Gertsev, V. V.; Zhurnal Vsesoyuznogo Khimicheskogo Obshchestva im. D. I. Mendeleeva; vol. 14; (1969); p. 352 - 353; C. A.; vol. 71; (1969); p. 80877 ; (from Gmelin) View in Reaxys in neat (no solvent) vol. B: B-Verb.13; 2.2.7, page 71 - 82 ; (from Gmelin) View in Reaxys

Al3+ 3

O

Cl

O

O

–O

Rx-ID: 692602 View in Reaxys 185/238

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

90/102

2018-05-09 18:36:04

Yield

Conditions & References With benzene Kuskow; Jur'ewa; Doklady Akademii Nauk SSSR; vol. 109; (1956); p. 319; Doklady Chemistry; 106-111 <1956> 389 View in Reaxys

O

O

O

O

O

Rx-ID: 555417 View in Reaxys 186/238 Yield

Conditions & References With oxygen, toluene-4-sulfonic acid, T= 90 °C Patent; Hercules Powder Co.; US2799698; (1954) View in Reaxys

O

O

HO

Rx-ID: 852614 View in Reaxys 187/238 Yield

Conditions & References With sulfuric acid, acetic anhydride Boehme; Schran; Chemische Berichte; vol. 82; (1949); p. 453,456, 458 View in Reaxys Meisenheimer; Chou; Justus Liebigs Annalen der Chemie; vol. 539; (1939); p. 78,83 View in Reaxys Edkins; Linnell; Quarterly Journal of Pharmacy and Pharmacology; vol. 9; (1936); p. 75,102 View in Reaxys With boric acid, toluene, unter Entfernen des entstehenden Wassers und Erhitzen des Reaktionsprodukts mit Essigsaeure Hirao; Yagi; Kogyo Kagaku Zasshi; vol. 56; (1953); p. 371; ; (1954); p. 10536 View in Reaxys Hirao; Yabuuti; Yakugaku Zasshi; vol. 74; (1954); p. 1073; ; 1055 11593 View in Reaxys

O

-1

O

O

(v1)

O

O

Cl

N Ag+ Cl O

O

O

O

O

O O

Rx-ID: 7447304 View in Reaxys 188/238 Yield

Conditions & References Burton; Munday; Journal of the Chemical Society; (1954); p. 1456,1459 View in Reaxys

Cl

O

O

O

HO

Rx-ID: 851188 View in Reaxys 189/238

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

91/102

2018-05-09 18:36:04

Yield

Conditions & References Rix; Arens; ; vol. 56; (1953); p. 368,370 View in Reaxys

O

O

OH

O

O

O

OH

Cl OO

O

O

O

O O

O O

Rx-ID: 7447305 View in Reaxys 190/238 Yield

Conditions & References Kuhn; Daxner; Monatshefte fuer Chemie; vol. 83; (1952); p. 689,693 View in Reaxys Burton; Praill; Journal of the Chemical Society; (1951); p. 522,528 View in Reaxys

O HN

O

O

O

Cl

O

Cl

O

H

Rx-ID: 359633 View in Reaxys 191/238 Yield

Conditions & References zeitlicher Verlauf der Reaktion McElvain; Tate; Journal of the American Chemical Society; vol. 73; (1951); p. 2233,2234 View in Reaxys

O

O N

O

O

O

O

O

Cl

AgClO4

O

O

O O

O O

Rx-ID: 7447306 View in Reaxys 192/238 Yield

Conditions & References Burton; Praill; Journal of the Chemical Society; (1951); p. 522,528 View in Reaxys

O

O

HO

O

O

O

Rx-ID: 715565 View in Reaxys 193/238 Yield

Conditions & References With chloroform, T= 23 - 26 °C Friess; Journal of the American Chemical Society; vol. 71; (1949); p. 14 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

92/102

2018-05-09 18:36:04

O

O

OH

O

O

Cl HO

P Cl

Cl

Rx-ID: 5958488 View in Reaxys 194/238 Yield

Conditions & References T= 100 °C Batra; Rozdon; Proceedings - Indian Academy of Sciences, Section A; nb. 29; (1949); p. 350; ; (1949); p. 9049 View in Reaxys

O

O

O

aqueous chloroform HO

O

O

Rx-ID: 5958491 View in Reaxys 195/238 Yield

Conditions & References T= 25 °C , Lichtausschluss Friess; Journal of the American Chemical Society; vol. 71; (1949); p. 14 View in Reaxys

O

O

OH

HO

O

P2O5

Rx-ID: 5958495 View in Reaxys 196/238 Yield

Conditions & References T= 100 °C Batra; Rozdon; Proceedings - Indian Academy of Sciences, Section A; nb. 29; (1949); p. 350; ; (1949); p. 9049 View in Reaxys O

water containing chloroform HO

O

O

O

O

Rx-ID: 6683467 View in Reaxys 197/238 Yield

Conditions & References unter Lichtausschluss Friess; Journal of the American Chemical Society; vol. 71; (1949); p. 14 View in Reaxys O

–

O

2

O

O

Hg 2+

2-acetoxy-cyclohexanone-(1)

O

Rx-ID: 8259884 View in Reaxys 198/238 Yield

Conditions & References Treibs; Bast; Justus Liebigs Annalen der Chemie; vol. 561; (1949); p. 165,170

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93/102

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View in Reaxys

O

O

Br

Rx-ID: 108345 View in Reaxys 199/238 Yield

Conditions & References With mercury(II) diacetate, T= 130 °C Koton; Sorina; Ossberg; Zhurnal Obshchei Khimii; vol. 17; (1947); p. 59,61; ; (1948); p. 141 View in Reaxys

–O

O

O

Hg 2+

2

Br

HgBr2

O

Rx-ID: 6728700 View in Reaxys 200/238 Yield

Conditions & References T= 130 °C Koton; Sorina; Ossberg; Zhurnal Obshchei Khimii; vol. 17; (1947); p. 59,61; ; (1948); p. 141 View in Reaxys

–O

O

O

Hg 2+

2

Br

O

Br2Hg

Rx-ID: 26159721 View in Reaxys 201/238 Yield

Conditions & References 130°C Koton, M. M.; Zorina, T. M.; Osberg, E. G.; Zhurnal Obshchei Khimii; vol. 17; (1947); p. 59 - 62 ; (from Gmelin) View in Reaxys 130°C vol. Hg: MVol.B3; 6.21.4, page 1276 - 1279 ; (from Gmelin) View in Reaxys O O

O

O

O

O

O

OH

Br

Rx-ID: 192240 View in Reaxys 202/238 Yield

Conditions & References McElvain; Fajardo-Pinzon; Journal of the American Chemical Society; vol. 67; (1945); p. 651 View in Reaxys

O O

O

O

Br

O

O

Br

Rx-ID: 462485 View in Reaxys 203/238

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

94/102

2018-05-09 18:36:04

Yield

Conditions & References Erhitzen unter Normaldruck McElvain; Fajardo-Pinzon; Journal of the American Chemical Society; vol. 67; (1945); p. 651 View in Reaxys

O O

O

O

HO

Rx-ID: 851466 View in Reaxys 204/238 Yield

Conditions & References With sulfuric acid Patent; Eastman Kodak Co.; US2422016; (1945) View in Reaxys

O O

O

O

Br

sodium phenolate (2 mol) Br

Rx-ID: 7063415 View in Reaxys 205/238 Yield

Conditions & References McElvain; Fajardo-Pinzon; Journal of the American Chemical Society; vol. 67; (1945); p. 651 View in Reaxys

O Cl

O

O

O

H

HO

Rx-ID: 7067231 View in Reaxys 206/238 Yield

Conditions & References McElvain; Fajardo-Pinzon; Journal of the American Chemical Society; vol. 67; (1945); p. 651 View in Reaxys

O

O

O

O

O

O

Rx-ID: 465802 View in Reaxys 207/238 Yield

Conditions & References Destillation unter Normaldruck McElvain; Kundiger; Journal of the American Chemical Society; vol. 64; (1942); p. 254,259 View in Reaxys

O

O

O

O

O

HO

S

O HO

Rx-ID: 625022 View in Reaxys 208/238 Yield

Conditions & References Hurd; Roe; Journal of the American Chemical Society; vol. 61; (1939); p. 3355,3357 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

95/102

2018-05-09 18:36:04

O

O

OH

O

O

HO

HO

S OO

Rx-ID: 6683465 View in Reaxys 209/238 Yield

Conditions & References Hurd; Roe; Journal of the American Chemical Society; vol. 61; (1939); p. 3355,3357 View in Reaxys

H 2N

O

O

O

HO

Rx-ID: 850856 View in Reaxys 210/238 Yield

Conditions & References With boron trifluoride Patent; du Pont de Nemours and Co.; US2036353; (1934) View in Reaxys Sowa; Nieuwland; Journal of the American Chemical Society; vol. 55; (1933); p. 5052 View in Reaxys Guareschi; Justus Liebigs Annalen der Chemie; vol. 171; (1874); p. 142 View in Reaxys Guareschi; Justus Liebigs Annalen der Chemie; vol. 171; (1874); p. 142 View in Reaxys

O

O

Br

O

O Br

O

O

O

O

O

Br

O

Rx-ID: 174214 View in Reaxys 211/238 Yield

Conditions & References T= 130 °C Berggardh; ; vol. 42; (1933); p. 76,77, 81; Chem. Zentralbl.; vol. 105; nb. I; (1934); p. 2267 View in Reaxys

O

Br

O

O

O O

O

O

O Br

O

O Br

Rx-ID: 174217 View in Reaxys 212/238 Yield

Conditions & References T= 120 °C

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Berggardh; ; vol. 42; (1933); p. 76,82; Chem. Zentralbl.; vol. 105; nb. I; (1934); p. 2267 View in Reaxys

–O

Br

O

O

Ag+

Br

O

Br

Rx-ID: 8259883 View in Reaxys 213/238 Yield

Conditions & References T= 20 °C Birckenbach; Goubeau; Chemische Berichte; vol. 66; (1933); p. 1285,1287 View in Reaxys

Cl

O

O –O

Cl

O

O Na

Cl

O

O

HO

O

OH

O

H 2N 2

+

O

O

Rx-ID: 468096 View in Reaxys 214/238 Yield

Conditions & References T= 140 - 150 °C Melnikow; Ssidorowa; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 740,742; Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2313 View in Reaxys

O –O

O

O

O

O

Na +

Rx-ID: 569832 View in Reaxys 215/238 Yield

Conditions & References With sodium hydroxide, T= 0 °C Chattaway; Journal of the Chemical Society; (1931); p. 2495 View in Reaxys Huber; Brunner; Chemische Berichte; vol. 56; (1930); p. 322,324 View in Reaxys

O

O

O

Br

Br

O

Br Br

Rx-ID: 666664 View in Reaxys 216/238 Yield

Conditions & References Lyden; ; vol. 38; (1929); p. 19 View in Reaxys

O

O

O

magnesium bromide-phenolate

Rx-ID: 5958494 View in Reaxys 217/238 Yield

Conditions & References With diethyl ether, folgend Hydrolyse Gilman; Schulze; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 756

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

97/102

2018-05-09 18:36:04

View in Reaxys

O

O

O

O

OH

HO

S OO

HO

Rx-ID: 6683464 View in Reaxys 218/238 Yield

Conditions & References Patent; Consort.electrochem.Ind.; DE578387; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 920 View in Reaxys

O

O

O

Cl –O

O

Na +

Rx-ID: 224737 View in Reaxys 219/238 Yield

Conditions & References With water Kirner; Journal of the American Chemical Society; vol. 48; (1926); p. 2748 View in Reaxys

O

O

O

Cl

H

H

–O

O

O

Na +

Rx-ID: 7063414 View in Reaxys 220/238 Yield

Conditions & References Kirner; Journal of the American Chemical Society; vol. 48; (1926); p. 2748 View in Reaxys

O

O

O

O

O

O

O

O

Rx-ID: 555203 View in Reaxys 221/238 Yield

Conditions & References Turner; Sheppard; Journal of the Chemical Society; vol. 127; (1925); p. 546 View in Reaxys Turner; Sheppard; Journal of the Chemical Society; vol. 127; (1925); p. 546 View in Reaxys

O O

OH

O O O

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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O

O

O

O

O

HO

O

OH

Rx-ID: 643103 View in Reaxys 222/238 Yield

Conditions & References Gelissen; Hermans; Chemische Berichte; vol. 58; (1925); p. 768 View in Reaxys

O

O

OH

O

dibenzoylperoxy

Rx-ID: 5958492 View in Reaxys 223/238 Yield

Conditions & References Gelissen; Hermans; Chemische Berichte; vol. 58; (1925); p. 768 View in Reaxys

O

H N

OH

N O

O O

H

H N

O

N H

HO

O

Rx-ID: 641095 View in Reaxys 224/238 Yield

Conditions & References Bergmann; Ulpts; Witte; Chemische Berichte; vol. 56; (1923); p. 682 View in Reaxys

O

H N

OH

O

O

N O

Rx-ID: 641096 View in Reaxys 225/238 Yield

Conditions & References Bergmann; Ulpts; Witte; Chemische Berichte; vol. 56; (1923); p. 682 View in Reaxys H N

O

O

N

Rx-ID: 22355864 View in Reaxys 226/238 Yield

Conditions & References Reaction Steps: 2 1: peroxybenzoic acid; diethyl ether With Perbenzoic acid, diethyl ether Bergmann; Ulpts; Witte; Chemische Berichte; vol. 56; (1923); p. 682 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

99/102

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O

O

O

HO

S O

O

O

OH

Rx-ID: 851593 View in Reaxys 227/238 Yield

Conditions & References With acetic acid van Peski; Recueil des Travaux Chimiques des Pays-Bas; vol. 40; (1921); p. 116 View in Reaxys

O

O

OH

HO

O

ZnCl2

o-oxy-acetophenone

Rx-ID: 6730233 View in Reaxys 228/238 Yield

Conditions & References Pauly; Lockemann; Chemische Berichte; vol. 48; (1915); p. 30 View in Reaxys

O

O

O

O

O

HO

Rx-ID: 572389 View in Reaxys 229/238 Yield

Conditions & References T= 100 °C Panow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 35; (1903); p. 97; Chem. Zentralbl.; vol. 74; nb. I; (1903); p. 1128 View in Reaxys Dobrochotow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 27; (1895); p. 345; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1895); p. 393 View in Reaxys

O

O

O

O

O

HO O

O

Rx-ID: 851219 View in Reaxys 230/238 Yield

Conditions & References Autenrieth; Chemische Berichte; vol. 34; (1901); p. 177 View in Reaxys

–

O

N

O

O

OH

O

O

+

N+

K

Rx-ID: 639009 View in Reaxys 231/238 Yield

Conditions & References beim Behandeln von Benzoldiazoniumchlorid Orndorff; American Chemical Journal; vol. 10; (1888); p. 368 View in Reaxys Hantzsch; Chemische Berichte; vol. 33; (1900); p. 2527,2535, 2536 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

100/102

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O

O

OH

N+

N

O

Cl

Rx-ID: 639010 View in Reaxys 232/238 Yield

Conditions & References beim Behandeln von Benzoldiazoniumchlorid, Product distribution Orndorff; American Chemical Journal; vol. 10; (1888); p. 368 View in Reaxys Hantzsch; Chemische Berichte; vol. 33; (1900); p. 2527,2535, 2536 View in Reaxys

O–

O N

O

O

OH

O

N

N+

O

Rx-ID: 641860 View in Reaxys 233/238 Yield

Conditions & References Orndorff; American Chemical Journal; vol. 10; (1888); p. 368 View in Reaxys O

O

Cl

2 HO

O

O

O

chlorohydroquinone monoacetate

Rx-ID: 8271124 View in Reaxys 234/238 Yield

Conditions & References Clermont; Chautard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 102; (1886); p. 1072 View in Reaxys

O –O

O

O Na +

O

O P

O

O

Rx-ID: 275353 View in Reaxys 235/238 Yield

Conditions & References Kreysler; Chemische Berichte; vol. 18; (1885); p. 1716 View in Reaxys

–

O

4

O

O Pb4+

O

HO

Rx-ID: 852315 View in Reaxys 236/238

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Yield

Conditions & References With carbon disulfide, T= 170 °C Broughton; Justus Liebigs Annalen der Chemie; vol. Suppl.4; (1865); p. 121 View in Reaxys

–O

O

O Pb4+

4

HO

O

CS2

Rx-ID: 6683466 View in Reaxys 237/238 Yield

Conditions & References T= 170 °C , im Druckrohr Broughton; Justus Liebigs Annalen der Chemie; vol. Suppl.4; (1865); p. 121 View in Reaxys

–O

O

O

O

K+

O

O P

O

O

Rx-ID: 275352 View in Reaxys 238/238 Yield

Conditions & References With ethanol Williamson; Justus Liebigs Annalen der Chemie; vol. 92; (1854); p. 317; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1854); p. 603 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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