alpha-Methylhydrocinnamic acid (2-Methyl-3-phenylpropanoic acid) [C10H12O2]

alpha-Methylhydrocinnamic acid [C10H12O2]

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68 reactions in Reaxys

2018-07-26 23h:52m:49s (UTC)

O

1. Query

HO

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='1009-67-2') AND (IDE.INCHI='MCIIDRLDHRQKPHUHFFFAOYSA-N') NOT (RX.RXRN=2046121))

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alpha-Methylhydrocinnamic acid [C10H12O2]

O

HO C

HO

O

O

Rx-ID: 47880099 View in Reaxys 1/68 Yield

Conditions & References With iron(III) trifluoromethanesulfonate, water, palladium diacetate, triphenylphosphine in 1,4-dioxane, Time= 15h, T= 120 °C , p= 37503.8Torr , Sealed tube, Inert atmosphere, Autoclave, Overall yield = 89 percent; regioselective reaction Huang, Zijun; Cheng, Yazhe; Chen, Xipeng; Wang, Hui-Fang; Du, Chen-Xia; Li, Yuehui; Chemical Communications; vol.

54; nb. 32; (2018); p. 3967 - 3970 View in Reaxys O

HO

O

HO

Rx-ID: 305307 View in Reaxys 2/68 Yield 99 %

Conditions & References With potassium hydroxide, hydrogen, polystyrene-poly(ethylene glycol), palladium in water, Time= 24h, T= 25 °C , p= 760Torr Nakao, Ryu; Rhee, Hakjune; Uozumi, Yasuhiro; Organic Letters; vol. 7; nb. 1; (2005); p. 163 - 165 View in Reaxys

97 %

4.6.1. General procedure for hydrogenations General procedure: 1.0 mmol, 0.148 g), catalyst BPPd(0)Si (5 molpercent, 0.0836 g), andKOH (1.0 equiv., 5 mL 0.2 M solution) were added to the reactionflask under hydrogen gas (1 atm). The reaction mixture was stirredat room temperature for 30 min followed by catalyst filtration andwashing with 10 mL of water and ethyl acetate. The pH was adjusted to 2e3 using 1 N HCl. The organic phase was collectedafter solvent extraction from ethyl acetate and dried over MgSO4and in vacuo. The product was purified by silica-gel column chromatographyand analyzed by 1H NMR spectroscopy.

With hydrogen, potassium hydroxide in water, Time= 1h, T= 20 °C , p= 760.051Torr , Green chemistry Shabbir, Saira; Lee, Sinyoung; Lim, Minkyung; Lee, Heejin; Ko, Hyeji; Lee, Youngbok; Rhee, Hakjune; Journal of Organometallic Chemistry; vol. 846; (2017); p. 296 - 304 View in Reaxys With hydrogen, <Rh(cycloocten)2Cl>2 in tetrahydrofuran, Time= 17h, p= 825.07Torr , Ambient temperature, cat. asymmetric hydrogenation; various times, solvents and mol-ratios of the catalysts; Li-derivative of C6H5C<=N-(S)-CH(CH3) (C6H5)>NHCH(CH3)(C6H5) as cocatalyst, Product distribution Brunner, Henri; Agrifoglio, Giuseppe; Monatshefte fuer Chemie; vol. 111; (1980); p. 275 - 287 View in Reaxys With nickel, T= 150 °C , p= 73550.8Torr , Hydrogenation Mastagli; Lambert; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 233; (1951); p. 751 View in Reaxys With sodium hydroxide, aluminum nickel Schrecker; Journal of Organic Chemistry; vol. 22; (1957); p. 33 View in Reaxys With acetic acid, platinum, Hydrogenation Woodruff; Conger; Journal of the American Chemical Society; vol. 60; (1938); p. 465 View in Reaxys With hydrogen, 10 wt. % palladium on activated carbon

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alpha-Methylhydrocinnamic acid [C10H12O2]

Somasekharan, K. N.; Kiefer, Edgar F.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 27; nb. 1-12; (1988); p. 29 - 37 View in Reaxys Yu; Simon; Tetrahedron; vol. 47; nb. 43; (1991); p. 9035 - 9052 View in Reaxys 99 % Chromat.

With ammonium formate, 1-butyl-3-methylimidazolium Tetrafluoroborate, palladium diacetate, Time= 5h, T= 65 °C Baan, Zoltan; Finta, Zoltan; Keglevich, Gyoergy; Hermecz, Istvan; Tetrahedron Letters; vol. 46; nb. 37; (2005); p. 6203 6204 View in Reaxys

97 % Spectr.

With hydrogen, polysilane-supported Pd in hexane, Time= 6h, T= 20 °C Oyamada, Hidekazu; Akiyama, Ryo; Hagio, Hiroyuki; Naito, Takeshi; Kobayashi, Shu; Chemical Communications; nb.

41; (2006); p. 4297 - 4299 View in Reaxys

99 % Chromat.

With ammonium formate, 1-butyl-3-methylimidazolium Tetrafluoroborate, magnesium-lanthanum mixed oxide, palladium, Time= 5h, T= 80 °C Baan, Zoltan; Potor, Attila; Cwik, Agnieszka; Hell, Zoltan; Keglevich, Gyoergy; Finta, Zoltan; Hermecz, Istvan; Synthetic Communications; vol. 38; nb. 10; (2008); p. 1601 - 1609 View in Reaxys O

O I

HO

HO

Rx-ID: 11048898 View in Reaxys 3/68 Yield

Conditions & References With lithium diisopropyl amide in tetrahydrofuran, T= -78 °C Zhang, Minsheng; Porte, Alex; Diamantidis, George; Sogi, Kimberly; Kubrak, Dennis; Resnick, Lynn; Mayer, Scott C.; Wang, Zheng; Kreft, Anthony F.; Harrison, Boyd L.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 9; (2007); p.

2401 - 2403 View in Reaxys Stage 1: With lithium diisopropyl amide in tetrahydrofuran, Time= 1h, T= -15 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Time= 4h, T= -15 - 20 °C , Inert atmosphere Hu, Jiantao; Lan, Tianlong; Sun, Yihua; Chen, Hui; Yao, Jiannian; Rao, Yu; Chemical Communications; vol. 51; nb. 80; (2015); p. 14929 - 14932 View in Reaxys Stage 1: With lithium diisopropyl amide in tetrahydrofuran, Time= 2h, T= 0 - 80 °C , Inert atmosphere Stage 2: in tetrahydrofuran, T= 0 - 80 °C Zhang, Zhuo-Zhuo; Han, Ye-Qiang; Zhan, Bei-Bei; Wang, Sai; Shi, Bing-Feng; Angewandte Chemie - International Edition; vol. 56; nb. 42; (2017); p. 13145 - 13149; Angew. Chem.; vol. 129; nb. 42; (2017); p. 13325 - 13329,5 View in Reaxys O

O

O

HO

Rx-ID: 46489631 View in Reaxys 4/68 Yield 42 %

Conditions & References With 1,2,2,6,6-pentamethylpiperidine, [1,1';4',1'']terphenyl, water in hexane, N,N-dimethyl-formamide, Time= 0.133333h, T= 35 - 38 °C , p= 760.051Torr , Schlenk technique, UV-irradiation, Flow reactor

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alpha-Methylhydrocinnamic acid [C10H12O2]

Seo, Hyowon; Liu, Aofei; Jamison, Timothy F.; Journal of the American Chemical Society; vol. 139; nb. 40; (2017); p. 13969 - 13972 View in Reaxys O

O

O

HO

Rx-ID: 46489634 View in Reaxys 5/68 Yield

Conditions & References

66 %

With 1,2,2,6,6-pentamethylpiperidine, [1,1';4',1'']terphenyl, water in hexane, N,N-dimethyl-formamide, Time= 0.133333h, T= 35 - 38 °C , p= 760.051Torr , Schlenk technique, UV-irradiation, Flow reactor Seo, Hyowon; Liu, Aofei; Jamison, Timothy F.; Journal of the American Chemical Society; vol. 139; nb. 40; (2017); p. 13969 - 13972 View in Reaxys O

O

O

HO

HO O

Rx-ID: 46719936 View in Reaxys 6/68 Yield

Conditions & References Stage 1: With 9-borabicyclo-[3.3.1]nonane dimer in 1,4-dioxane, Time= 16h, T= 65 °C Stage 2: With copper(l) iodide, 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene hydrochloride, cesium fluoride, Time= 16h, T= 120 °C Stage 3: With hydrogenchloride in water Juhl, Martin; Laursen, Simon L. R.; Huang, Yuxing; Nielsen, Dennis U.; Daasbjerg, Kim; Skrydstrup, Troels; ACS Catalysis; vol. 7; nb. 2; (2017); p. 1392 - 1396 View in Reaxys O

HO

Rx-ID: 7250394 View in Reaxys 7/68 Yield 99%

Conditions & References 1 : EXAMPLE 1 The benzylmethylmalonic acid (49.2 g) was dissolved in 400 ml of acetonitrile with 1.69 g of cuprous oxide and heated to reflux for 5 hours.

The solvent was removed under vacuum.

The residue was taken up in 400 ml of diethyl ether and rinsed with 10percent hydrochloric acid (*300 ml), 300 ml of saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated.

The residue was purified by flash chromatography (5percentto 10percent methanol in chloroform) to yield 38.3 g of 2-benzylpropionic acid (99percent yield).

Patent; Merrell Pharmaceuticals Inc.; US5840729; (1998); (A) English View in Reaxys

99%

1 : EXAMPLE 1 The benzylmethylmalonic acid (49.2 g) was dissolved in 400 ml of acetonitrile with 1.69 g of cuprous oxide and heated to reflux for 5 hours.

The solvent was removed under vacuum.

The residue was taken up in 400 ml of diethyl ether and rinsed with 10percent hydrochloric acid (2*300 ml), 300 ml of saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated.

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alpha-Methylhydrocinnamic acid [C10H12O2]

The residue was purified by flash chromatography (5percentando10percent methanol in chloroform) to yield 38.3 g of 2-benzylpropionic acid (99percent yield).

Patent; Merrell Dow Pharmaceuticals Inc.; US5047534; (1991); (A) English View in Reaxys 99%

8 : EXAMPLE 8 The benzylmethylmalonic acid (49.2 g) was dissolved in 400 ml of acetonitrile, treated with 1.69 g of cuprous oxide and heated to reflux for 5 hours.

The solvent was removed under vacuum and the residue taken up in 400 ml of diethyl ether and rinsed with 10percent hydrochloric acid (2*300 ml), saturated sodium chloride (300 ml), dried over magnesium sulfate, filtered and concentrated.

The residue was purified by flash chromatography (5percent to 10percent methanol in chloroform) to yield 38.37 g of 2-benzylpropionic acid (99percent yield).

Patent; Merrell Dow Pharmaceuticals Inc.; US5047534; (1991); (A) English View in Reaxys Patent; Merrell Pharmaceuticals Inc.; US5840729; (1998); (A) English View in Reaxys Reinheckel,H.; Tauber,G.; Monatshefte fuer Chemie; vol. 98; (1967); p. 1944 - 1953 View in Reaxys Patent; Farbwerke Hoechst A.G.; DE1300565; (1965); ; vol. 71; nb. 91098t; (1969) View in Reaxys Harmon et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 3684 View in Reaxys Normant; Angelo; Bulletin de la Societe Chimique de France; (1962); p. 814 View in Reaxys Hjelte; Acta Chemica Scandinavica (1947-1973); vol. 15; (1961); p. 1200 View in Reaxys Spassov; Stefanova; Journal of Molecular Structure; vol. 53; (1979); p. 219,220,223 View in Reaxys Larcheveque; Annales de Chimie (Cachan, France); vol. 5; nb. 14; (1970); p. 129,132 View in Reaxys Kuchar et al.; Collection of Czechoslovak Chemical Communications; vol. 44; (1979); p. 183,186 View in Reaxys Aviron-Violet et al.; Journal of Molecular Catalysis; vol. 5; (1979); p. 44; ; vol. 91; nb. 57462k View in Reaxys Aguiar et al.; Journal of Organic Chemistry; vol. 41; nb. 9; (1976); p. 1545,1547 View in Reaxys Byers; Wolfenden; Biochemistry; vol. 12; nb. 11; (1973); p. 2070 - 2078 View in Reaxys Marvell et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 608,610 View in Reaxys Marshall et al.; Journal of Organic Chemistry; vol. 31; (1966); p. 4315,4317 View in Reaxys Horner et al.; Liebigs Annalen der Chemie; (1979); p. 341,351 View in Reaxys Pastuschak; Dombrowskii; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 3110,3150 View in Reaxys Gossauer; Ossorio; Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica; vol. 59; (1963); p. 185,189 View in Reaxys Larcheveque; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 268; (1969); p. 640 View in Reaxys 8 : EXAMPLE 8 After six additional recrystallizations from 50percent aqueous ethanol there remained 18.8 g of the quinine salt.

The mother liquors from the above recrystallizations were acidified and extracted to yield 24.86 g of recovered 2-benzylpropionic acid.

Patent; Merrell Dow Pharmaceuticals Inc.; US5047534; (1991); (A) English View in Reaxys Patent; Merrell Pharmaceuticals Inc.; US5840729; (1998); (A) English

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alpha-Methylhydrocinnamic acid [C10H12O2]

View in Reaxys 2.2 : Preparation of phenylpropionic acid General procedure: Under the air atmosphere, the weigh 2-(3-phenylpropionamido)- pyridine-1-oxide (0.2 mmol), Sodium hydroxide 120mg(3 mmol), was placed in 10 mL of Shrek tube then 1 mL of anhydrous ethanol was added and reacted at 90 ° C for 24h. After completion of the reaction, the mixture was cooled to room temperature, 30 mL of a mol / L dilute hydrochloric acid solution was added, and extracted with 30 mL (3 x 10 mL) of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The resulting material was separated and purified by column chromatography (eluent: dichloromethane: methanol = 1: 10) to give pure Phenylpropionic acid 23.8 mg, 80percent; With sodium hydroxide in ethanol, Time= 24h, T= 90 °C Patent; Zhengzhou University; NIU, JUNLONG; YANG, XINYAN; HAO, XINQI; ZHANG, LINBAO; ZHAO, XUEMEI; REN, BAOZENG; SONG, MAOPING; (9 pag.); CN104592006; (2016); (B) Chinese View in Reaxys

O

HO

N O S

S O

O

O

Rx-ID: 38621032 View in Reaxys 8/68 Yield

Conditions & References

95 %

With sodium in ethanol, Time= 14h, T= 20 °C , Inert atmosphere Hussein, Waleed M.; McGeary, Ross P.; Australian Journal of Chemistry; vol. 67; nb. 8-9; (2014); p. 1222 - 1227 View in Reaxys

O

O

O

HO

Rx-ID: 39113141 View in Reaxys 9/68 Yield

Conditions & References

87 %

With camphor-10-sulfonic acid, dihydrogen peroxide in ethyl acetate, Time= 1h, T= 20 °C Yu, Xin; Liu, Zheng; Xia, Zilei; Shen, Zhigao; Pan, Xixian; Zhang, Hui; Xie, Weiqing; RSC Advances; vol. 4; nb. 96; (2014); p. 53397 - 53401 View in Reaxys O

HO

O

HO

Rx-ID: 305298 View in Reaxys 10/68 Yield 98 %

Conditions & References With hydrogen, potassium hydroxide in water, Time= 0.5h, T= 20 °C , p= 760.051Torr , Sealed tube Lim, Minkyung; De Castro, Kathlia A.; Oh, Seungchan; Lee, Kangsuk; Chang, Young-Wook; Kim, Hokun; Rhee, Hakjune; Applied Organometallic Chemistry; vol. 25; nb. 1; (2011); p. 1 - 8 View in Reaxys

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alpha-Methylhydrocinnamic acid [C10H12O2]

86.50 %

With methanol, magnesium Verma, Raman K.; Singla, Rubina; Punniyakoti; Medicinal Chemistry Research; vol. 13; nb. 8-9; (2004); p. 660 - 676 View in Reaxys

68.2 %

With potassium hydroxide, hydrogen, [RhCl(Ph3P)2], Ph2PO2CCH=CMe2 in acetone, Time= 17h, T= 22 °C , p= 2280Torr Preston, Sheila A.; Cupertino, Domenico C.; Palma-Ramirez, Pilar; Cole-Hamilton, David J.; Journal of the Chemical Society, Chemical Communications; nb. 12; (1986); p. 977 - 978 View in Reaxys With hydrogen, triethylamine, <Rh(PPh3)2(Ph2PO2CCMe=CHPh)>PF6 in tetrahydrofuran, Time= 20h, p= 2280Torr , Ambient temperature, various catalysts, other bases; other substituted propenoic acids and hexene, Product distribution, Mechanism Iraqi, Ahmed; Fairfax, Neil R.; Preston, Sheila A.; Cupertino, Domenico C.; Irvine, Derek J.; Cole-Hamilton, David J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 8; (1991); p. 1929 - 1936 View in Reaxys With Wilkinson's catalyst, ammonium formate in water, dimethyl sulfoxide, Time= 0.0833333h, Irradiation, also without microwave irradiation in var. temp.; also 2H labelled formate salts; also cinnamic acid, Product distribution Al-Qahtani, Mohammed H.; Cleator, Nicola; Danks, Timothy N.; Garman, Russell N.; Jones, John R.; Stefaniak, Stefan; Morgan, Alan D.; Simmonds, Alan J.; Journal of Chemical Research - Part S; nb. 7; (1998); p. 400 - 401 View in Reaxys With sodium amalgam, ethanol Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 180 View in Reaxys With sodium hydroxide, nickel Watson,M.B.; Youngson,G.W.; Journal of the Chemical Society [Section] C: Organic; (1968); p. 258 - 262 View in Reaxys With hydrogen, triethylamine, <RhCl(PPh3)2(PH2PO2CCMe=CHPh)> in tetrahydrofuran, Time= 20h, p= 2280Torr , Ambient temperature, Yield given Iraqi, Ahmed; Fairfax, Neil R.; Preston, Sheila A.; Cupertino, Domenico C.; Irvine, Derek J.; Cole-Hamilton, David J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 8; (1991); p. 1929 - 1936 View in Reaxys 60.b : b b α-Methyl-hydrocinnamic acid A solution of α-methyl cinnamic acid (10.0 g., 61.7 mmol.) in dry methanol (250 ml.) was treated with 10percent palladium on carbon and hydrogenated (balloon used) at room temperature for 16 hours.

The reaction mixture was diluted with methanol (250 ml.), filtered through a Celite pad in a millipore unit, washing the pad well with methanol (2*100 ml.).

The clear filtrate was evaporated to dryness to give 10.225 g. of title product as a thick syrup.

With palladium in methanol Patent; E. R. Squibb and Sons, Inc.; US5552397; (1996); (A) English View in Reaxys 25 :27 mg (71 micromol) of Rh(NBD)(acac) was mixed with 4 ml of acetone in a small Schlenk flask. To the resulting clear solution was added 0.11 ml of a stock solution prepared by adding 0.1 ml of neat 54percent wt tetrafluoroboric acid in diethylether to 1 ml of acetone (1.02 eq), resulting in a red solution. After 1 minute, 20 microlitre (1 eq) of norbornadiene was added by syringe. 0.5 ml aliquots containing 9 micromoles of cationic Rh-complex was added to ligand samples as detailed in the table. Clear yellow to red solutions were obtained and aliquots were analysed by 31P NMR adding some d6 acetone. 31P NMR showed a virtually complete consumption of the ligand and formation of cationic Rh-complexes. 4 samples of 0.32 g of α-methylcinnamic acid were weighed into 4 glass liners of the Biotage Endeavour screening unit and to each was added 4 ml of acetone.

After the addition of the catalyst solutions, the acetone solutions were purged several times with nitrogen. Hydrogenation at a substrate to catalyst ratio 200 /1 was carried out at 250C and 15 bar for 60 hours, giving conversions as indicated in the table.

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alpha-Methylhydrocinnamic acid [C10H12O2]

With hydrogen, mixture of Rh(NBD)(acac), HBF4, norbornadiene and Selke Ph-α-GLUP phosphine in diethyl ether, acetone, Time= 60h, T= 25 °C , p= 11251.1Torr , Product distribution / selectivity Patent; JOHNSON MATTHEY PUBLIC LIMITED COMPANY; NEDDEN, Hans Guenter; WO2010/1173; (2010); (A1) English View in Reaxys 2.98 g

With 10% palladium on activated carbon; Degussa type, hydrogen in ethanol, Time= 5h, T= 20 °C , Inert atmosphere Sasmal, Aniruddha; Taniguchi, Tsuyoshi; Wipf, Peter; Curran, Dennis P.; Canadian Journal of Chemistry; vol. 91; nb. 1; (2013); p. 1 - 5 View in Reaxys 5.1.4 General procedure B: the synthesis of propanoic acid derivative from acrylic acid by Pd/C-catalyzed reduction General procedure: A mixture of acrylic acid (55 mmol, 1.0 equiv) and Pd/C (10percent) in methanol (70 mL) was hydrogenated under 10 atm of hydrogen for 24 h. The catalyst was filtered off and the filtrate concentrated to afford propanoic acid, which was used in the next step as it was. An analytical sample of compound was obtained by flash column chromatography on silica gel With 10% palladium on activated carbon; Degussa type, hydrogen in methanol, Time= 24h, p= 7600.51Torr Wang, Zhi-Gang; Chen, Liqun; Chen, Jiebo; Zheng, Jian-Feng; Gao, Weiwei; Zeng, Zhiping; Zhou, Hu; Zhang, XiaoKun; Huang, Pei-Qiang; Su, Ying; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 632 - 648 View in Reaxys O

O

HO

O

Rx-ID: 1992712 View in Reaxys 11/68 Yield 100 %

Conditions & References General procedure for the hydrolase-catalysed kinetic resolution of the 3-aryl alkanoic ethyl esters 2a–c (analytical scale) General procedure: A spatula tip of enzyme (α5–10mg, amount not critical) was added to the ester substrate 2a–c (α50mg) in a 0.1M phosphate buffer, pH 7 (4.5mL). The small test tubes were sealed and agitated at 700–750rpm and incubated for the appropriate length of time and temperature. The aqueous layer was extracted with diethyl ether (3×5mL) and the combined organic extracts were filtered through Celite® and concentrated under reduced pressure. The sample was analysed by 1H NMR spectroscopy, reconcentrated and dissolved in a mixture of isopropanol/hexane [10:90 (HPLC grade)]. The enantioselectivity was determined by chiral HPLC. The results of the screens are summarised in Tables 1 and 3.

With candida antarctica B lipase (immob) in aq. phosphate buffer, Time= 20h, T= 20 °C , pH= 7, Resolution of racemate, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Deasy, Rebecca E.; Moody, Thomas S.; Maguire, Anita R.; Tetrahedron Asymmetry; vol. 24; nb. 23; (2013); p. 1480 - 1487 View in Reaxys

74 %

With water, hydroxide in ethanol, Time= 5h, Heating Knorr, Rudolf; Lattke, Ernst; Chemische Berichte; vol. 114; nb. 6; (1981); p. 2116 - 2131 View in Reaxys With potassium hydroxide Crombie, Aimee L.; Kane Jr., John L.; Shea, Kevin M.; Danheiser, Rick L.; Journal of Organic Chemistry; vol. 69; nb. 25; (2004); p. 8652 - 8667 View in Reaxys With potassium hydroxide, water John L Jr., Kane; Shea, Kevin M.; Crombie, Aimee L.; Danheiser, Rick L.; Organic Letters; vol. 3; nb. 7; (2001); p. 1081 1084 View in Reaxys

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alpha-Methylhydrocinnamic acid [C10H12O2]

O H

HO O

Rx-ID: 21852832 View in Reaxys 12/68 Yield

Conditions & References Reaction Steps: 3 1: 90 percent / Zn, I2 / benzene; diethyl ether / 3 h / Heating 2: 85 percent / Et3SiH, BF3-Et2O / CH2Cl2 / 1 h / 0 °C 3: 95 percent / aq. NaOH / methanol / 1 h / Heating With triethylsilane, sodium hydroxide, boron trifluoride diethyl etherate, iodine, zinc in methanol, diethyl ether, dichloromethane, benzene Smonou, Ioulia; Orfanopoulos, Michael; Synthetic Communications; vol. 20; nb. 9; (1990); p. 1387 - 1397 View in Reaxys Reaction Steps: 2 1.1: potassium carbonate / 0.08 h / 0 °C 1.2: 12 h / 160 - 180 °C 2.1: 10% palladium on activated carbon; Degussa type; hydrogen / methanol / 24 h / 7600.51 Torr With 10% palladium on activated carbon; Degussa type, hydrogen, potassium carbonate in methanol, 1.1: |Perkin Carboxylic Acid Synthesis / 1.2: |Perkin Carboxylic Acid Synthesis Wang, Zhi-Gang; Chen, Liqun; Chen, Jiebo; Zheng, Jian-Feng; Gao, Weiwei; Zeng, Zhiping; Zhou, Hu; Zhang, XiaoKun; Huang, Pei-Qiang; Su, Ying; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 632 - 648 View in Reaxys O

O

O

O

O

O

HO H

O

H

Rx-ID: 36990118 View in Reaxys 13/68 Yield

Conditions & References General procedure for the hydrolase-catalysed kinetic resolution of the 3-aryl alkanoic ethyl esters 2a–c (analytical scale) General procedure: A spatula tip of enzyme (α5–10mg, amount not critical) was added to the ester substrate 2a–c (α50mg) in a 0.1M phosphate buffer, pH 7 (4.5mL). The small test tubes were sealed and agitated at 700–750rpm and incubated for the appropriate length of time and temperature. The aqueous layer was extracted with diethyl ether (3×5mL) and the combined organic extracts were filtered through Celite® and concentrated under reduced pressure. The sample was analysed by 1H NMR spectroscopy, reconcentrated and dissolved in a mixture of isopropanol/hexane [10:90 (HPLC grade)]. The enantioselectivity was determined by chiral HPLC. The results of the screens are summarised in Tables 1 and 3.

With Mucor meihei hydrolase in aq. phosphate buffer, Time= 20h, T= 20 °C , pH= 7, Resolution of racemate, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Deasy, Rebecca E.; Moody, Thomas S.; Maguire, Anita R.; Tetrahedron Asymmetry; vol. 24; nb. 23; (2013); p. 1480 - 1487 View in Reaxys

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alpha-Methylhydrocinnamic acid [C10H12O2]

O

O

O

HO

Rx-ID: 29239361 View in Reaxys 14/68 Yield

Conditions & References

1.31 g

With trifluoroacetic acid in dichloromethane, Time= 0.5h, T= 30 °C Davies, Stephen G.; Goodwin, Christopher J.; Hepworth, David; Roberts, Paul M.; Thomson, James E.; Journal of Organic Chemistry; vol. 75; nb. 4; (2010); p. 1214 - 1227 View in Reaxys

O

HO

O

O

O F

F

F F

F F

Rx-ID: 28576586 View in Reaxys 15/68 Yield

Conditions & References Stage 1: With lithium hydroxide, water in tetrahydrofuran, methanol, Time= 12h, T= 20 °C Stage 2: With water, sodium hydrogencarbonate Stage 3: With hydrogenchloride in water Broeker, Joachim; Knollmueller, Max; Gaertner, Peter; Tetrahedron Asymmetry; vol. 20; nb. 3; (2009); p. 273 - 287 View in Reaxys

O

O

HO

O

O

O

O

O

Rx-ID: 28576587 View in Reaxys 16/68 Yield

Conditions & References Stage 1: With lithium hydroxide, water in tetrahydrofuran, methanol, Time= 12h, T= 20 °C Stage 2: With water, sodium hydrogencarbonate Stage 3: With hydrogenchloride in water

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10/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

Broeker, Joachim; Knollmueller, Max; Gaertner, Peter; Tetrahedron Asymmetry; vol. 20; nb. 3; (2009); p. 273 - 287 View in Reaxys

O

O

O

HO

O

O O

Pol (v1)

Rx-ID: 28576615 View in Reaxys 17/68 Yield

Conditions & References Stage 1: With lithium hydroxide, water in tetrahydrofuran, methanol, Time= 96h, T= 20 °C , solid phase reaction Stage 2: With water, sodium hydrogencarbonate in tetrahydrofuran, methanol, solid phase reaction Stage 3: With hydrogenchloride in water, Cooling with ice, solid phase reaction, optical yield given as percent ee Broeker, Joachim; Knollmueller, Max; Gaertner, Peter; Tetrahedron Asymmetry; vol. 20; nb. 3; (2009); p. 273 - 287 View in Reaxys

O

O

O

HO

O

O O

O

Pol (v1)

Rx-ID: 28576616 View in Reaxys 18/68 Yield 49 %

Conditions & References Stage 1: With lithium hydroxide, water in tetrahydrofuran, methanol, Time= 96h, T= 20 °C , solid phase reaction Stage 2: With water, sodium hydrogencarbonate in tetrahydrofuran, methanol, solid phase reaction Stage 3: With hydrogenchloride in water, Cooling with ice, solid phase reaction, optical yield given as percent ee Broeker, Joachim; Knollmueller, Max; Gaertner, Peter; Tetrahedron Asymmetry; vol. 20; nb. 3; (2009); p. 273 - 287 View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

11/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

O

HO O

O

O

O

O

Rx-ID: 28576617 View in Reaxys 19/68 Yield

Conditions & References

82 %

Stage 1: With lithium hydroxide, water in tetrahydrofuran, methanol, Time= 12h, T= 20 °C Stage 2: With water, sodium hydrogencarbonate Stage 3: With hydrogenchloride in water Broeker, Joachim; Knollmueller, Max; Gaertner, Peter; Tetrahedron Asymmetry; vol. 20; nb. 3; (2009); p. 273 - 287 View in Reaxys

O

HO

O

O

O

Rx-ID: 28576624 View in Reaxys 20/68 Yield

Conditions & References Stage 1: With lithium hydroxide, water in tetrahydrofuran, methanol, Time= 12h, T= 20 °C Stage 2: With water, sodium hydrogencarbonate Stage 3: With hydrogenchloride in water Broeker, Joachim; Knollmueller, Max; Gaertner, Peter; Tetrahedron Asymmetry; vol. 20; nb. 3; (2009); p. 273 - 287 View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

12/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

O

HO

O O

O

O O

Rx-ID: 28576625 View in Reaxys 21/68 Yield

Conditions & References Stage 1: With lithium hydroxide, water in tetrahydrofuran, methanol, Time= 12h, T= 20 °C Stage 2: With water, sodium hydrogencarbonate Stage 3: With hydrogenchloride in water Broeker, Joachim; Knollmueller, Max; Gaertner, Peter; Tetrahedron Asymmetry; vol. 20; nb. 3; (2009); p. 273 - 287 View in Reaxys OH

O

O HO

O

OH

Rx-ID: 765947 View in Reaxys 22/68 Yield 95 %

Conditions & References With copper(I) oxide in acetonitrile, Time= 6h, Heating Toussaint, Olivier; Capdevielle, Patrice; Maumy, Michel; Synthesis; nb. 12; (1986); p. 1029 - 1031 View in Reaxys Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 178 View in Reaxys (decarboxylation) Terashima,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 18; (1970); p. 1124 - 1136 View in Reaxys in N,N-dimethyl-formamide, Time= 4h, T= 100 - 110 °C Colombo, M.; Amici, M. De; Micheli, C. De; Pitre, D.; Carrea, G.; Riva, S.; Tetrahedron: Asymmetry; vol. 2; nb. 10; (1991); p. 1021 - 1030 View in Reaxys With sulfuric acid, Time= 1h, Heating, Yield given Tyrrell, Elizabeth; Tsang, Michael W. H.; Skinner, George A.; Fawcett, John; Tetrahedron; vol. 52; nb. 29; (1996); p. 9841 9852 View in Reaxys With sulfuric acid, Time= 3h, Heating Dib; Ibrahim; Al-Awadi; International Journal of Chemical Kinetics; vol. 40; nb. 2; (2008); p. 51 - 58 View in Reaxys

16.5 g

Time= 2h, T= 170 °C

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13/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

Alcalde, Ermitas; Mesquida, Neus; Frigola, Jordi; Lopez-Perez, Sara; Merce, Ramon; Organic and Biomolecular Chemistry; vol. 6; nb. 20; (2008); p. 3795 - 3810 View in Reaxys O

(1R,2R)-O-Merrifield bound N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2'-phenylacetamide

Br

HO

Rx-ID: 13176314 View in Reaxys 23/68 Yield

Conditions & References Reaction Steps: 2 1: LDA / tetrahydrofuran 2: aq. KOH With potassium hydroxide, lithium diisopropyl amide in tetrahydrofuran Crombie, Aimee L.; Kane Jr., John L.; Shea, Kevin M.; Danheiser, Rick L.; Journal of Organic Chemistry; vol. 69; nb. 25; (2004); p. 8652 - 8667 View in Reaxys O

O

HO

O

Rx-ID: 2042017 View in Reaxys 24/68 Yield

Conditions & References

100 %

With potassium hydroxide in ethanol, water, Time= 8h, T= 0 °C Kato, Dai-Ichiro; Mitsuda, Satoshi; Ohta, Hiromichi; Journal of Organic Chemistry; vol. 68; nb. 19; (2003); p. 7234 - 7242 View in Reaxys

95 %

With sodium hydroxide in methanol, Time= 1h, Heating Smonou, Ioulia; Orfanopoulos, Michael; Synthetic Communications; vol. 20; nb. 9; (1990); p. 1387 - 1397 View in Reaxys O

O

HO

O

Rx-ID: 14077256 View in Reaxys 25/68 Yield

Conditions & References Reaction Steps: 2 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: 47 percent / tetrahydrofuran; hexane / 0.5 h / 0 °C 2.1: 100 percent / potassium hydroxide / ethanol; H2O / 8 h / 0 °C With potassium hydroxide, n-butyllithium, diisopropylamine in tetrahydrofuran, ethanol, hexane, water Kato, Dai-Ichiro; Mitsuda, Satoshi; Ohta, Hiromichi; Journal of Organic Chemistry; vol. 68; nb. 19; (2003); p. 7234 - 7242 View in Reaxys

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14/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

O

polymer-bound NMe3 (1+)*SCN(1-)

HO

Br

Rx-ID: 15507334 View in Reaxys 26/68 Yield

Conditions & References Reaction Steps: 2 1: LDA / tetrahydrofuran 2: KOH; H2O With potassium hydroxide, water, lithium diisopropyl amide in tetrahydrofuran John L Jr., Kane; Shea, Kevin M.; Crombie, Aimee L.; Danheiser, Rick L.; Organic Letters; vol. 3; nb. 7; (2001); p. 1081 1084 View in Reaxys

O

O

HO

N

Rx-ID: 8648162 View in Reaxys 27/68 Yield

Conditions & References With hydrogenchloride, Hydrolysis Chandrasekhar, Sosale; Kausar, Amina; Tetrahedron Asymmetry; vol. 11; nb. 11; (2000); p. 2249 - 2253 View in Reaxys O

HO

HO

Li O

Rx-ID: 5061704 View in Reaxys 28/68 Yield

Conditions & References

12 %

in tetrahydrofuran, Time= 2h, T= -70 °C , Addition Aurell, Maria Jose; Domingo, Luis Ramon; Mestres, Ramon; Munos, Elena; Zaragoza, Ramon Jose; Tetrahedron; vol. 55; nb. 3; (1999); p. 815 - 830 View in Reaxys

O

O

O

HO

Rx-ID: 4818648 View in Reaxys 29/68 Yield 89 %

Conditions & References With oxonium in tetrahydrofuran, T= 100 °C Suprun; Advanced Synthesis and Catalysis; vol. 340; nb. 3; (1998); p. 247 - 255 View in Reaxys

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15/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

O O

O

OH

O

HO

HO

O O

O

O O

Rx-ID: 4575471 View in Reaxys 30/68 Yield

Conditions & References

5 %, 2 %, 9 With manganese triacetate, Time= 22h, T= 60 °C % Chromat.

Jamie, Joanne F.; Rickards, Rodney W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 21; (1996); p. 2603 2613 View in Reaxys O

O

O

HO

HO

O O

O

O O

Rx-ID: 4586308 View in Reaxys 31/68 Yield

Conditions & References

5 %, 2 %, 9 With manganese triacetate, acetic acid, Time= 22h, T= 60 °C % Chromat.

Jamie, Joanne F.; Rickards, Rodney W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 21; (1996); p. 2603 2613 View in Reaxys O

Br

potassium-compound of propionic acid-<1-methyl-2-oxo-propylidenehydrazide>

HO

Rx-ID: 17508389 View in Reaxys 32/68 Yield

Conditions & References Reaction Steps: 2 1: 80 percent / LDA / tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) r.t., 1 h 2: 5 percent / manganese(III) acetate / 22 h / 60 °C With manganese triacetate, lithium diisopropyl amide in tetrahydrofuran Jamie, Joanne F.; Rickards, Rodney W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 21; (1996); p. 2603 2613 View in Reaxys Reaction Steps: 2 1: 80 percent / LDA / tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) r.t., 1 h

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alpha-Methylhydrocinnamic acid [C10H12O2]

2: 5 percent / manganese(III) acetate, acetic acid / 22 h / 60 °C With manganese triacetate, acetic acid, lithium diisopropyl amide in tetrahydrofuran Jamie, Joanne F.; Rickards, Rodney W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 21; (1996); p. 2603 2613 View in Reaxys O

C O

Br

HO

Rx-ID: 17758483 View in Reaxys 33/68 Yield

Conditions & References Reaction Steps: 3 1: 1.) NaOEt / 1.) EtOH, 30 min, 2.) EtOH, reflux, 2 h 2: aq. KOH / 1 h / Heating 3: conc. H2SO4 / 1 h / Heating With potassium hydroxide, sulfuric acid, sodium ethanolate Tyrrell, Elizabeth; Tsang, Michael W. H.; Skinner, George A.; Fawcett, John; Tetrahedron; vol. 52; nb. 29; (1996); p. 9841 9852 View in Reaxys

O

O

HO

O O O

Rx-ID: 17763424 View in Reaxys 34/68 Yield

Conditions & References Reaction Steps: 2 1: aq. KOH / 1 h / Heating 2: conc. H2SO4 / 1 h / Heating With potassium hydroxide, sulfuric acid Tyrrell, Elizabeth; Tsang, Michael W. H.; Skinner, George A.; Fawcett, John; Tetrahedron; vol. 52; nb. 29; (1996); p. 9841 9852 View in Reaxys Reaction Steps: 2 1: aq. KOH / ethanol / 24 h / Heating 2: dimethylformamide / 4 h / 100 - 110 °C With potassium hydroxide in ethanol, N,N-dimethyl-formamide Colombo, M.; Amici, M. De; Micheli, C. De; Pitre, D.; Carrea, G.; Riva, S.; Tetrahedron: Asymmetry; vol. 2; nb. 10; (1991); p. 1021 - 1030 View in Reaxys Reaction Steps: 2 1: concentrated aqueous KOH-solution With potassium hydroxide Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 178 View in Reaxys

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17/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

O

O

O

O

HO

S

O

O

O

O

O

Rx-ID: 4271420 View in Reaxys 35/68 Yield

Conditions & References With potassium hydroxide, sodium hydride, 1.) THF, 3 h, room temp., 2.) H2O, room temp., 3.) 190 deg C, Yield given. Multistep reaction Bucher; Linden; Heimgartner; Helvetica Chimica Acta; vol. 78; nb. 4; (1995); p. 935 - 946 View in Reaxys O

HO Cl

Rx-ID: 21039728 View in Reaxys 36/68 Yield

Conditions & References Reaction Steps: 3 1: 1.) NaH / 1.) ethyl ether, reflux, 2.) ethyl ether, RT, 6 h 2: aq. KOH / ethanol / 24 h / Heating 3: dimethylformamide / 4 h / 100 - 110 °C With potassium hydroxide, sodium hydride in ethanol, N,N-dimethyl-formamide Colombo, M.; Amici, M. De; Micheli, C. De; Pitre, D.; Carrea, G.; Riva, S.; Tetrahedron: Asymmetry; vol. 2; nb. 10; (1991); p. 1021 - 1030 View in Reaxys Reaction Steps: 3 2: concentrated aqueous KOH-solution With potassium hydroxide Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 178 View in Reaxys O

O

OH

HO

O

Rx-ID: 21824188 View in Reaxys 37/68 Yield

Conditions & References Reaction Steps: 2 1: 85 percent / Et3SiH, BF3-Et2O / CH2Cl2 / 1 h / 0 °C 2: 95 percent / aq. NaOH / methanol / 1 h / Heating With triethylsilane, sodium hydroxide, boron trifluoride diethyl etherate in methanol, dichloromethane Smonou, Ioulia; Orfanopoulos, Michael; Synthetic Communications; vol. 20; nb. 9; (1990); p. 1387 - 1397 View in Reaxys

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18/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

O P

O (v1)

HO

Cu

O

Rx-ID: 1522269 View in Reaxys 38/68 Yield

Conditions & References

67 %

in diethyl ether, Time= 1.5h, T= -78 °C Kawashima, Masatoshi; Sato, Toshio; Fujisawa, Tamotsu; Tetrahedron; vol. 45; nb. 2; (1989); p. 403 - 412 View in Reaxys O

O HO

Rx-ID: 2063579 View in Reaxys 39/68 Yield

Conditions & References

80 %

With potassium permanganate Nalesnik, Theodore E.; Freudenberger, John H.; Orchin, Milton; Journal of Organometallic Chemistry; vol. 221; nb. 2; (1981); p. 193 - 198 View in Reaxys O

O

O

O

O

Cl

HO

O

O

O

Rx-ID: 3917528 View in Reaxys 40/68 Yield

Conditions & References With aluminium trichloride, Ambient temperature, Mechanism, Product distribution Pinnick, Harold W.; Brown, Stephen P.; McLean, Elizabeth A.; Zoller, Linwood W.; Journal of Organic Chemistry; vol. 46; nb. 18; (1981); p. 3758 - 3760 View in Reaxys O

O HO

Rx-ID: 18527359 View in Reaxys 41/68 Yield

Conditions & References Reaction Steps: 2 1: 96 percent / NaOAc, PPh3, H2, RhCl(PPh3) / benzene / 24 h / 110 °C / 103430 Torr 2: 80 percent / KMnO4 With potassium permanganate, [RhCl(PPh3)], hydrogen, sodium acetate, triphenylphosphine in benzene Nalesnik, Theodore E.; Freudenberger, John H.; Orchin, Milton; Journal of Organometallic Chemistry; vol. 221; nb. 2; (1981); p. 193 - 198

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19/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

View in Reaxys O

disodium-compound of 1,1,2,2-tetraphenyl-ethane

HO

Cl

Rx-ID: 20638978 View in Reaxys 42/68 Yield

Conditions & References Reaction Steps: 2 1: 52 percent / NaOEt / ethanol / 5 h / Heating 2: 74 percent / H2O/OH- / ethanol / 5 h / Heating With water, hydroxide, sodium ethanolate in ethanol Knorr, Rudolf; Lattke, Ernst; Chemische Berichte; vol. 114; nb. 6; (1981); p. 2116 - 2131 View in Reaxys O O

Br–

HO

+Mg

O

Rx-ID: 1522267 View in Reaxys 43/68 Yield

Conditions & References

52 %

With copper(l) chloride in tetrahydrofuran, Time= 0.25h, T= 0 °C Sato, Toshio; Kawara, Tatsuo; Kawashima, Masatoshi; Fujisawa, Tamotsu; Chemistry Letters; (1980); p. 571 - 574 View in Reaxys O

HO HO Cl

O

Rx-ID: 2696287 View in Reaxys 44/68 Yield

Conditions & References With n-butyllithium, diisopropylamine, 1) THF, -60 deg C to room temp., 30 min; 2) THF, -40 deg C to 20 deg C, Yield given.

Multistep reaction Boche, Gernot; Buckl, Klaus; Martens, Diether; Schneider, Dieter R.; Liebigs Annalen der Chemie; nb. 7; (1980); p. 1135 1171 View in Reaxys O O

Ph2CuMgBr

HO

O

Rx-ID: 7250401 View in Reaxys 45/68 Yield 52 %

Conditions & References in tetrahydrofuran, 1.) -30 deg C, 1 h, 2.) 0 deg C, 1 h Fujisawa, Tamotsu; Sato, Toshio; Kawara, Tatsuo; Kawashima, Masatoshi; Tetrahedron Letters; vol. 21; (1980); p. 2181 2184 View in Reaxys

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20/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

O

O

HO

O

Rx-ID: 1041842 View in Reaxys 46/68 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide in methanol Cocker,W.; Grayson,D.H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1975); p. 1347 - 1352 View in Reaxys

O

HO

I

O

N

Rx-ID: 1433633 View in Reaxys 47/68 Yield

Conditions & References (i) nBuLi, (ii) /BRN= 969135/, (iii) aq. HCl, Multistep reaction Meyers,A.I. et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 2778 - 2783 View in Reaxys O O

O HO

I

Cl

O

O

Rx-ID: 1203266 View in Reaxys 48/68 Yield

Conditions & References Kashiwagi,T. et al.; Tetrahedron; vol. 26; (1970); p. 3619 - 3629 View in Reaxys

O

O

S

HO

P

O

O

Rx-ID: 1340292 View in Reaxys 49/68 Yield

Conditions & References (i) Raney-Ni, THF, (ii) KOH, aq. EtOH, (iii) H2, Raney-Ni, aq. MeOH, Multistep reaction Bestmann,H.J. et al.; Chemische Berichte; vol. 99; (1966); p. 1906 - 1911 View in Reaxys

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21/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

O Cl

O

O

HO

Rx-ID: 1046610 View in Reaxys 50/68 Yield

Conditions & References With magnesium in diethyl ether Urry,W.H. et al.; Journal of Organic Chemistry; vol. 29; nb. 7; (1964); p. 1663 - 1669 View in Reaxys O

HO

HO

Rx-ID: 22518041 View in Reaxys 51/68 Yield

Conditions & References Reaction Steps: 2 1: SOCl2 2: Mg / diethyl ether With thionyl chloride, magnesium in diethyl ether Urry,W.H. et al.; Journal of Organic Chemistry; vol. 29; nb. 7; (1964); p. 1663 - 1669 View in Reaxys O

HO

(+-)-2-chloro-2-methyl-3-phenyl-propionic acid methyl ester

Rx-ID: 7250397 View in Reaxys 52/68 Yield

Conditions & References With acetic acid, zinc Dombrowskii et al.; Zhurnal Obshchei Khimii; vol. 27; (1957); p. 419; engl. Ausg. S. 473 View in Reaxys O

(+-)-2-benzyl-2-methyl-acetoacetic acid ethyl ester

HO

Rx-ID: 7250396 View in Reaxys 53/68 Yield

Conditions & References With barium dihydroxide Shinya; Nippon Nogei Kagaku Kaishi; vol. 29; (1955); p. 91,92; ; (1959); p. 1227 View in Reaxys

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22/26

2018-07-26 23:55:36

alpha-Methylhydrocinnamic acid [C10H12O2]

O

O –O

HO

HO

Na +

O

O

Rx-ID: 55936 View in Reaxys 54/68 Yield

Conditions & References Behandeln des danach isolierten Reaktionsprodukts mit wss. Natronlauge Patent; Kay-Fries Chem. Inc.; US2413493; (1941) View in Reaxys O

O –

O

HO

Na +

O

O

Rx-ID: 470487 View in Reaxys 55/68 Yield

Conditions & References With methanol, Behandeln des Reaktionsprodukts mit wss. Natronlauge Patent; Kay-Fries Chem. Inc.; US2413493; (1941) View in Reaxys O

(+-)-2-methyl-3-phenyl-propionaldehyde

HO

Rx-ID: 7250398 View in Reaxys 56/68 Yield

Conditions & References With iron isobutyrate, oxygen, isobutyric Acid, T= 30 °C Patent; Shell Devel. Co.; US2010358; (1933) View in Reaxys O

O

HO

HO

aqueous solution of sodium-salt

Rx-ID: 7250400 View in Reaxys 57/68 Yield

Conditions & References With sodium amalgam, Hydrogenation Holden; Lapworth; Journal of the Chemical Society; (1931); p. 2368,2375 View in Reaxys O

O

HO HO

sodium amalgam Br Br

Rx-ID: 7987452 View in Reaxys 58/68 Yield

Conditions & References Simonsen; Journal of the Chemical Society; vol. 117; (1920); p. 569

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23/26

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alpha-Methylhydrocinnamic acid [C10H12O2]

View in Reaxys

O

O

Br

O OH HO

HO

O

O HO

Rx-ID: 472551 View in Reaxys 59/68 Yield

Conditions & References With magnesium, nachfolgend Verseifen Salkind; Grabowski; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 46; (1914); p. 505; Chem. Zentralbl.; vol. 85; nb. II; (1914); p. 1270 View in Reaxys O

Br

O

I

O

O

I

magnesium

O OH HO

HO

O HO

Rx-ID: 8202788 View in Reaxys 60/68 Yield

Conditions & References nachfolgend Verseifen des Reaktionsproduktes Salkind; Grabowski; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 46; (1914); p. 505; Chem. Zentralbl.; vol. 85; nb. II; (1914); p. 1270 View in Reaxys O

OH

O

sodium

O

HO HO

Rx-ID: 7047562 View in Reaxys 61/68 Yield

Conditions & References v. Braun; Grabowski; Kirschbaum; Chemische Berichte; vol. 46; (1913); p. 1280

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24/26

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alpha-Methylhydrocinnamic acid [C10H12O2]

View in Reaxys NH 2

O

O

O

HO

Rx-ID: 796180 View in Reaxys 62/68 Yield

Conditions & References With yellow aqueous ammonium sulfide, T= 200 °C , unter Druck Willgerodt; Merk; Journal fuer Praktische Chemie (Leipzig); vol. <2> 80; (1909); p. 193 View in Reaxys NH 2

O

O

yellow aqueous ammonium sulfide

O

HO

Rx-ID: 5815025 View in Reaxys 63/68 Yield

Conditions & References T= 200 °C , unter Druck Willgerodt; Merk; Journal fuer Praktische Chemie (Leipzig); vol. <2> 80; (1909); p. 193 View in Reaxys O

HO HO

Rx-ID: 317273 View in Reaxys 64/68 Yield

Conditions & References With chromic acid, acetic acid Guerbet; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 945; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 866 View in Reaxys Guerbet; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 146; (1908); p. 1406; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 944; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 866 View in Reaxys With potassium carbonate, T= 230 °C , im geschlossenen Rohr Guerbet; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 945; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 866 View in Reaxys Guerbet; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 146; (1908); p. 1406; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 944; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 866 View in Reaxys bei der Oxydation Guerbet; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 146; (1908); p. 300,1405 View in Reaxys Guerbet; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 504,943; Chem. Zentralbl.; vol. 79; nb. II; (1908); p.

866 View in Reaxys

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25/26

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alpha-Methylhydrocinnamic acid [C10H12O2]

O

O HO

air

Rx-ID: 7250399 View in Reaxys 65/68 Yield

Conditions & References v. Miller; Rohde; Chemische Berichte; vol. 23; (1890); p. 1080 View in Reaxys OH

O

O

O

O

HO

O

OH

Rx-ID: 5809826 View in Reaxys 66/68 Yield

Conditions & References Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 178 View in Reaxys O

HO

α-methyl-α-benzyl-acetoacetic acid ethyl ester

Rx-ID: 7250395 View in Reaxys 67/68 Yield

Conditions & References With potassium hydroxide Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 180 View in Reaxys

O

O

concentrated KOH-solution

HO

O

O

Rx-ID: 7987451 View in Reaxys 68/68 Yield

Conditions & References Bischoff; Conrad; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 179,180 View in Reaxys

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