gamma-Butyrolactone (oxolan-2-one; dihydrofuran-2(3H)-one; GBL)

Reaxys

PubChem

eMolecules

Reactions (367)

Yield

Substances (27)

Citations (530)

Conditions

References

1

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98%

With trans-{dioxoruthenium(VI)(N,N'-dimethyl-N,N'-bis(2pyridylmethyl)propylenediamine)}(perchlorate)2 in acetonitrile

T=25°C; 1 h;

Che, Chi-Ming; Tang, Wai-Tong; Li, Chi-Keung

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1990 , # 12 p. 3735 - 3739 Title/Abstract

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98%

Stage #1: With bromine in dichloromethane; water

1 h; Reflux; Stage #2: With dihydrogen peroxide in dichloromethane; water

1 h; Reflux;

Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene

Organic Process Research and Development, 1998 , vol. 2, # 4 p. 261 - 269 Title/Abstract

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86%

With manganese (VII)-oxide in tetrachloromethane; acetone

T=-45°C;

Troemel, Martin; Russ, Manuel

Angewandte Chemie, 1987 , vol. 99, # 10 p. 1037 - 1038 Title/Abstract

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85%

With trans-lt;Ru(VI)(dmpipy)2O2gt;lt;ClO4gt;2 in acetonitrile

4 h; Ambient temperature;

Che, Chi-Ming; Leung, Wai-Ho; Li, Chi-Keung; Poon, Chung-Kwong

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1991 , # 3 p. 379 - 384

Title/Abstract

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80%

With lt;RuVL(O)gt;2+-complex lt;HL = lt;2-hydroxy-2-(2pyridyl)ethylgt;bislt;2-(2-pyridyl)ethylgt;aminegt; in acetonitrile

Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1991 , # 5 p. 1259 - 1263 Title/Abstract

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80%

With potassium permanganate; iron(III) chloride in acetone

T=-78 - 20°C; 15 h;

Lai, Sheng; Lee, Donald G.

Tetrahedron, 2002 , vol. 58, # 49 p. 9879 - 9887 Title/Abstract

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70%

With zinc dichromate(VI) in dichloromethane

1 h; Ambient temperature;

Firouzabadi, H.; Sardarian, A. R.; Moosavipour, H.; Afshari, G. M.

Synthesis, 1986 , # 4 p. 285 - 288 Title/Abstract

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70%

With aluminum oxide; potassium permanganate; copper(II) sulfate

T=20°C; 6 h;

Shaabani, Ahmad; Lee, Donald G.

Tetrahedron Letters, 2001 , vol. 42, # 34 p. 5833 - 5836 Title/Abstract

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68%

With calcium hypochlorite in water; acetic acid; acetonitrile

T=0°C; 1 h;

Nwaukwa, Stephen O.; Keehn, Philip M.

Tetrahedron Letters, 1982 , vol. 23, p. 35 - 38 Title/Abstract

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68%

With sodium bromate; sodium hydrogensulfite in water

T=20°C; Oxidation; 16.25 h;

Sakaguchi, Satoshi; Kikuchi, Daisuke; Ishii, Yasutaka

Bulletin of the Chemical Society of Japan, 1997 , vol. 70, # 10 p. 2561 - 2566 Title/Abstract

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67%

With sodium bromate; hydrogen bromide in dichloromethane

T=35°C; 5 h;

Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Yamasaki, Hiromochi; Fujisaki, Shizuo

Bulletin of the Chemical Society of Japan, 1986 , vol. 59, # 3 p. 747 - 750 Title/Abstract

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67%

With disodium hydrogenphosphate; benzyltrimethylammonium tribromide in water

T=60°C; 10 h;

Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo

Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 8 p. 2585 - 2588 Title/Abstract

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65%

With ruthenium tetroxide in tetrachloromethane

24 h; Ambient temperature;

Smith, Amos B.; Scarborough, Robert M.

Synthetic Communications, 1980 , vol. 10, # 3 p. 205 - 212 Title/Abstract

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65%

With chromium(VI) oxide; Salpetersaeuretrimethylsilylester in acetonitrile

24 h; Ambient temperature;

Shahi, Shatrughan P.; Gupta, Anuradha; Pitre, Sangeeta V.; Venkat Ram Reddy; Kumareswaran; Vankar, Yashwant D.

Journal of Organic Chemistry, 1999 , vol. 64, # 12 p. 4509 - 4511 Title/Abstract

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55%

With TS-1 (titanium silicate); dihydrogen peroxide

T=70°C; 12 h;

Sasidharan; Suresh; Sudalai

Tetrahedron Letters, 1995 , vol. 36, # 49 p. 9071 - 9072 Title/Abstract

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50%

Stage #1: With N -hydroxyphthalimide; 2,2'azobis(isobutyronitrile); oxygen in acetonitrile

T=65°C; P=760.051 Torr; 20 h; Stage #2: With sulfuric acid in acetonitrile

T=60°C; 4 h; Further stages.;

Fukuda, Osamu; Sakaguchi, Satoshi; Ishii, Yasutaka

Advanced Synthesis and Catalysis, 2001 , vol. 343, # 8 p. 809 - 813 Title/Abstract

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50%

Stage #1: With [bis(acetoxy)iodo]benzene in nitromethane

T=0°C; Stage #2: With tert.-butylhydroperoxide in decane; nitromethane

T=0 - 25°C; 12 h;

Zhao, Yi; Ang, Jascelyn Qian Lin; Ng, Angela Wan Ting; Yeung, Ying-Yeung

RSC Advances, 2013 , vol. 3, # 43 p. 19765 - 19768 Title/Abstract

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41%

With cis-lt;RuVI(6,6'-Cl2bpy)2O2gt;lt;ClO4gt; in acetonitrile

T=25°C; 1.5 h;

Che, Chi-Ming; Leung, Wai-Ho

Journal of the Chemical Society, Chemical Communications, 1987 , # 18 p. 1376 - 1377 Title/Abstract

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34%

With peroxomonophosphoric acid

T=25°C; 2 h; MeCN, p-benzoquinone; other ethers; Product distributionMechanism;

Ogata, Yoshiro; Tomizawa, Kohtaro; Ikeda, Toshiyuki

Journal of Organic Chemistry, 1980 , vol. 45, # 7 p. 1320 - 1322 Title/Abstract

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34%

With peroxomonophosphoric acid

T=25°C; 2 h;

Ogata, Yoshiro; Tomizawa, Kohtaro; Ikeda, Toshiyuki

Journal of Organic Chemistry, 1980 , vol. 45, # 7 p. 1320 - 1322 Title/Abstract

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28.8%

With C19H15ClFeN3O5; dihydrogen peroxide in ethyl acetate

24 h; Reagent/catalystSolventTime; Hide Experimental Procedure

Bhowon, Minu Gupta; Jhaumeer-Laulloo, Sabina; Wah, Henri Li Kam; Meetun, Anisha; Mudhoo, Karishma

Asian Journal of Chemistry, 2017 , vol. 29, # 1 p. 152 - 156 Title/Abstract

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Oxidation of tetrahydrofuran

The oxidation of tetrahydrofuran with the iron complex (1) gave no appreciable yieldof α-butyro-lactone with O2 and t-BuOOH. However, the 28.8 percent yield was noted with the combination of 1/H2O2/ethyl acetateafter 24 h, which decreases considerably with time. Comparedto iron complex (1), ruthenium complex (2) gave α-butyrolactone with only t-BuOOH but in poor yield (0.7-2.2 percent) (Table-3).

11%

With N -hydroxyphthalimide in pyridine

anodic oxidation;

Masui, Masaichiro; Hara, Seijiro; Ueshima, Takahiro; Kawaguchi, Tetsuo; Ozaki, Shigeko

Chemical & Pharmaceutical Bulletin, 1983 , vol. 31, # 11 p. 4209 - 4212 Title/Abstract

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9.5%

With iron(II) triflate; 2-((4R,5R)-1-((4-(tertbutyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2yl)pyridine; oxygen

T=60°C; P=760.051 Torr; 24 h; Green chemistry; Catalytic behavior; TimeTemperatureReagent/catalyst; chemoselective reaction;

Gonzalez-De-Castro, Angela; Robertson, Craig M.; Xiao, Jianliang

Journal of the American Chemical Society, 2014 , vol. 136, # 23 p. 8350 - 8360 Title/Abstract

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6%

With sodium periodate; RuCl3*2.9H2O in water

T=20°C; 1 h; Sonication;

Rup, Sandrine; Sindt, Michele; Oget, Nicolas

Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3123 - 3126 Title/Abstract

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With lt;RuVL(O)gt;2+-complex lt;HL = lt;2-hydroxy-2-(2pyridyl)ethylgt;bislt;2-(2-pyridyl)ethylgt;aminegt; in perchloric acid

T=24.9°C; ΔH(excit.), ΔS(excit.); MechanismRate constant;

Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1991 , # 5 p. 1259 - 1263 Title/Abstract

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With trans-lt;RuL1O2gt;2+ (L1 = 6,7,14,15,16,17,18,19-octahydro14,18-dimethyl-13Hdibenzolt;e,ngt;lt;1,4,8,12gt;dioxadiazacyclopentadecine; water in trifluoroacetic acid

T=24.9°C; ΔH(excit.), ΔS(excit.); other object of study: kinetic isotope effect; other conditions: other reagents; Rate constantThermodynamic dataMechanism;

Che, Chi-Ming; Tang, Wai-Tong; Wong, Kwok-Yin; Li, Chi-Keung

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1991 , # 12 p. 3277 - 3280 Title/Abstract

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With cobalt(III) acetylacetonate; oxygen; dimethylglyoxal

T=50°C; P=760 Torr; 6 h; other tetrahydrofuranes; var. αdiketones; also with Co(II), Fe(III), Ni(II) acetylacetonates;

Hata, Eiichiro; Takai, Toshihiro; Mukaiyama, Teruaki

Chemistry Letters, 1993 , # 9 p. 1513 - 1516 Title/Abstract

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With nitric acid; benzene

T=25°C;

Moschkin

Trudy Sovesc. Vopr. Ispolz. Pentozan. Syria RigaChem.Abstr., 1955 , p. 225,244 Trudy Sovesc. Vopr. Ispolz. Pentozan. Syria RigaChem.Abstr., 1959 , p. 15048 Full Text Show Details

With nitrogen; water

T=280°C; P=147102 Torr; beim Behandeln mit einem KupferoxidChromoxid-Katalysator;

BASF

Patent: DE849104 , 1950 ; DRP/DRBP Org.Chem.

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With water; hydrogen

T=280°C; P=147102 Torr; beim Behandeln mit einem KupferoxidChromoxid-Katalysator;

BASF

Patent: DE849104 , 1950 ; DRP/DRBP Org.Chem.

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60 % Chromat.

With hydrogenchloride; carbon dioxide; oxygen; copper dichloride; palladium dichloride

T=25°C; P=18240 Torr;

El'man, A. R.; Slivinskii, E. V.; Loktev, S. M.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1988 , vol. 37, p. 1969 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1988 , # 9 p. 2188 - 2189 Title/Abstract

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51 % Turnov.

With zinc(II) permanganate; silica gel in dichloromethane

T=20°C; 0.25 h;

Wolfe, Saul; Ingold, Christopher F.

Journal of the American Chemical Society, 1983 , vol. 105, # 26 p. 7755 - 7757 Title/Abstract

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60 % Chromat.

With cobalt(III) acetylacetonate; oxygen; dimethylglyoxal

T=50°C; P=760 Torr; 6 h;

Hata, Eiichiro; Takai, Toshihiro; Mukaiyama, Teruaki

Chemistry Letters, 1993 , # 9 p. 1513 - 1516 Title/Abstract

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33 % Chromat.

With tert.-butylhydroperoxide; trans-diaquabis(2,2'-bipyridineN,N')ruthenium(II) bis(hexafluorophosphate) in benzene

5 h; Ambient temperature;

Bailey, Alan J.; Griffith, William P.; Savage, Paul D.

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1995 , # 21 p. 3537 - 3542 Title/Abstract

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With oxygen; benzil

T=0°C; 6 h; Irradiation; Yield given;

Seto, Hideharu; Yoshida, Keigo; Yoshida, Shigeo; Shimizu, Takeshi; Seki, Hiroshi; Hoshino, Mikio

Tetrahedron Letters, 1996 , vol. 37, # 24 p. 4179 - 4182 Title/Abstract

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With oxygen; Ind(CO)3Mo-Ru(CO)2Cp

P=375.038 Torr; 168 h; Hide Experimental Procedure

HELSINKI UNIVERSITY OF TECHNOLOGY

Patent: WO2004/33391 A1, 2004 ; Location in patent: Page 4-5 ; Title/Abstract

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A:Catalytic runs; Table A. Oxidation of THF under various conditions

In a typical catalytic run, 0.1 mmol of the catalyst precursor was dissolved in 30 ml of dry THF and stirred under atmospheres of [OS,] [OS/CO] (1 [: 1)] and [02/C02] (1 [: 1)] respectively, which were supplied by balloon. The control runs under Ar, CO and C02 were carried out in sealed Schlenk flasks under a pressure of 0. [5] bar. The reactions were monitored by IR spectroscopy and the amounts of y-butyrolactone formed were derived from reference calibration (area for the v-CO band at 1780 [CM~1).] A rough quantitative approximation of the sum of all other products was obtained by reference to [PROPYLFORMATE] calibration (area for the v-CO band at 1726 [CM-APOS;,] relevant for all formed CO compounds other than y-butyrolactone). Fractional distillation of the reaction mixture of a typical 3 + [OS] run allowed us to isolate the pure products y- butyrolactone, succinic acid and [PROPYLFORMATE] as well as to quantify the sum of all other products. The formate acetal 6 [10] and others were detected in the mother solution and mixed fractions (NMR) but were not isolated. The organic compounds were identified by comparison of spectral data with literature results and/or authentic samples.

With carbon monoxide; oxygen; [Ru(CO)2Cp]2

P=375.038 Torr; 168 - 360 h; Hide Experimental Procedure

HELSINKI UNIVERSITY OF TECHNOLOGY

Patent: WO2004/33391 A1, 2004 ; Location in patent: Page 4-5 ; Title/Abstract

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A:Catalytic runs; Table A. Oxidation of THF under various conditions

In a typical catalytic run, 0.1 mmol of the catalyst precursor was dissolved in 30 ml of dry THF and stirred under atmospheres of [OS,] [OS/CO] (1 [: 1)] and [02/C02] (1 [: 1)] respectively, which were supplied by balloon. The control runs under Ar, CO and C02 were carried out in sealed Schlenk flasks under a pressure of 0. [5] bar. The reactions were monitored by IR spectroscopy and the amounts of y-butyrolactone formed were derived from reference calibration (area for the v-CO band at 1780 [CM~1).] A rough quantitative approximation of the sum of all other products was obtained by reference to [PROPYLFORMATE] calibration (area for the v-CO band at 1726 [CM-APOS;,] relevant for all formed CO compounds other than y-butyrolactone). Fractional distillation of the reaction mixture of a typical 3 + [OS] run allowed us to isolate the pure products y- butyrolactone, succinic acid and [PROPYLFORMATE] as well as to quantify the sum of all other products. The formate acetal 6 [10] and others were detected in the mother solution and mixed fractions (NMR) but were not isolated. The organic compounds were identified by comparison of spectral data with literature results and/or authentic samples

With carbon dioxide; oxygen; [Ru(CO)2Cp]2

P=375.038 Torr; 168 - 360 h; Hide Experimental Procedure

HELSINKI UNIVERSITY OF TECHNOLOGY

Patent: WO2004/33391 A1, 2004 ; Location in patent: Page 4-5 ; Title/Abstract

Full Text Show Details

A:Catalytic runs; Table A. Oxidation of THF under various conditions

In a typical catalytic run, 0.1 mmol of the catalyst precursor was dissolved in 30 ml of dry THF and stirred under atmospheres of [OS,] [OS/CO] (1 [: 1)] and [02/C02] (1 [: 1)] respectively, which were supplied by balloon. The control runs under Ar, CO and C02 were carried out in sealed Schlenk flasks under a pressure of 0. [5] bar. The reactions were monitored by IR spectroscopy and the amounts of y-butyrolactone formed were derived from reference calibration (area for the v-CO band at 1780 [CM~1).] A rough quantitative approximation of the sum of all other products was obtained by reference to [PROPYLFORMATE] calibration (area for the v-CO band at 1726 [CM-APOS;,] relevant for all formed CO compounds other than y-butyrolactone). Fractional distillation of the reaction mixture of a typical 3 + [OS] run allowed us to isolate the pure products y- butyrolactone, succinic acid and [PROPYLFORMATE] as well as to quantify the sum of all other products. The formate acetal 6 [10] and others were detected in the mother solution and mixed fractions (NMR) but were not isolated. The organic compounds were identified by comparison of spectral data with literature results and/or authentic samples

With oxygen; ruthenium(III)chloride

P=375.038 Torr; 168 - 360 h; Hide Experimental Procedure

HELSINKI UNIVERSITY OF TECHNOLOGY

Patent: WO2004/33391 A1, 2004 ; Location in patent: Page 4-5 ; Title/Abstract

Full Text Show Details

A:Catalytic runs; Table A. Oxidation of THF under various conditions

In a typical catalytic run, 0.1 mmol of the catalyst precursor was dissolved in 30 ml of dry THF and stirred under atmospheres of [OS,] [OS/CO] (1 [: 1)] and [02/C02] (1 [: 1)] respectively, which were supplied by balloon. The control runs under Ar, CO and C02 were carried out in sealed Schlenk flasks under a pressure of 0. [5] bar. The reactions were monitored by IR spectroscopy and the amounts of y-butyrolactone formed were derived from reference calibration (area for the v-CO band at 1780 [CM~1).] A rough quantitative approximation of the sum of all other products was obtained by reference to [PROPYLFORMATE] calibration (area for the v-CO band at 1726 [CM-APOS;,] relevant for all formed CO compounds other than y-butyrolactone). Fractional distillation of the reaction mixture of a typical 3 + [OS] run allowed us to isolate the pure products y- butyrolactone, succinic acid and [PROPYLFORMATE] as well as to quantify the sum of all other products. The formate acetal 6 [10] and others were detected in the mother solution and mixed fractions (NMR) but were not isolated. The organic compounds were identified by comparison of spectral data with literature results and/or authentic samples.

With oxygen; Cp(CO)3Mo-Ru(CO)2Cp

P=375.038 Torr; 168 - 360 h; Hide Experimental Procedure

HELSINKI UNIVERSITY OF TECHNOLOGY

Patent: WO2004/33391 A1, 2004 ; Location in patent: Page 4-5 ; Title/Abstract

Full Text Show Details

A:Catalytic runs; Table A. Oxidation of THF under various conditions

In a typical catalytic run, 0.1 mmol of the catalyst precursor was dissolved in 30 ml of dry THF and stirred under atmospheres of [OS,] [OS/CO] (1 [: 1)] and [02/C02] (1 [: 1)] respectively, which were supplied by balloon. The control runs under Ar, CO and C02 were carried out in sealed Schlenk flasks under a pressure of 0. [5] bar. The reactions were monitored by IR spectroscopy and the amounts of y-butyrolactone formed were derived from reference calibration (area for the v-CO band at 1780 [CM~1).] A rough quantitative approximation of the sum of all other products was obtained by reference to [PROPYLFORMATE] calibration (area for the v-CO band at 1726 [CM-APOS;,] relevant for all formed CO compounds other than y-butyrolactone). Fractional distillation of the reaction mixture of a typical 3 + [OS] run allowed us to isolate the pure products y- butyrolactone, succinic acid and [PROPYLFORMATE] as well as to quantify the sum of all other products. The formate acetal 6 [10] and others were detected in the mother solution and mixed fractions (NMR) but were not isolated. The organic compounds were identified by comparison of spectral data with literature results and/or authentic samples.

With oxygen; [Ru(CO)2Cp]2

P=375.038 Torr; 168 - 360 h; Hide Experimental Procedure

HELSINKI UNIVERSITY OF TECHNOLOGY

Patent: WO2004/33391 A1, 2004 ; Location in patent: Page 4-5 ; Title/Abstract

Full Text Show Details

A:Catalytic runs; Table A. Oxidation of THF under various conditions

In a typical catalytic run, 0.1 mmol of the catalyst precursor was dissolved in 30 ml of dry THF and stirred under atmospheres of [OS,] [OS/CO] (1 [: 1)] and [02/C02] (1 [: 1)] respectively, which were supplied by balloon. The control runs under Ar, CO and C02 were carried out in sealed Schlenk flasks under a pressure of 0. [5] bar. The reactions were monitored by IR spectroscopy and the amounts of y-butyrolactone formed were derived from reference calibration (area for the v-CO band at 1780 [CM~1).] A rough quantitative approximation of the sum of all other products was obtained by reference to [PROPYLFORMATE] calibration (area for the v-CO band at 1726 [CM-APOS;,] relevant for all formed CO compounds other than y-butyrolactone). Fractional distillation of the reaction mixture of a typical 3 + [OS] run allowed us to isolate the pure products y- butyrolactone, succinic acid and [PROPYLFORMATE] as well as to quantify the sum of all other products. The formate acetal 6 [10] and others were detected in the mother solution and mixed fractions (NMR) but were not isolated. The organic compounds were identified by comparison of spectral data with literature results and/or authentic samples.

With oxygen; Cp(CO)3Mo-Mo(CO)3Cp

P=375.038 Torr; 168 - 360 h; Hide Experimental Procedure

HELSINKI UNIVERSITY OF TECHNOLOGY

Patent: WO2004/33391 A1, 2004 ; Location in patent: Page 4-5 ; Title/Abstract

Full Text Show Details

A:Catalytic runs; Table A. Oxidation of THF under various conditions

In a typical catalytic run, 0.1 mmol of the catalyst precursor was dissolved in 30 ml of dry THF and stirred under atmospheres of [OS,] [OS/CO] (1 [: 1)] and [02/C02] (1 [: 1)] respectively, which were supplied by balloon. The control runs under Ar, CO and C02 were carried out in sealed Schlenk flasks under a pressure of 0. [5] bar. The reactions were monitored by IR spectroscopy and the amounts of y-butyrolactone formed were derived from reference calibration (area for the v-CO band at 1780 [CM~1).] A rough quantitative approximation of the sum of all other products was obtained by reference to [PROPYLFORMATE] calibration (area for the v-CO band at 1726 [CM-APOS;,] relevant for all formed CO compounds other than y-butyrolactone). Fractional distillation of the reaction mixture of a typical 3 + [OS] run allowed us to isolate the pure products y- butyrolactone, succinic acid and [PROPYLFORMATE] as well as to quantify the sum of all other products. The formate acetal 6 [10] and others were detected in the mother solution and mixed fractions (NMR) but were not isolated. The organic compounds were identified by comparison of spectral data with literature results and/or authentic samples.

41 %Chromat.

With [FeII(N,N'-(bis(2-pyridylmethyl)-(S,S)-2,2'-bipyrrolidine)) (CH3CN)2](SbF6)2; dihydrogen peroxide; acetic acid in acetonitrile

T=25°C; 0.5 h; regioselective reaction;

Chen, Mark S.; White, M. Christina

Science, 2010 , vol. 327, # 5965 p. 533 - 571 Title/Abstract

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72 %Spectr.

With ceric ammonium nitrate; C10H19IrO3(1-)*H(1+)*H2O4S in water-d2

T=21°C; 0.333333 h; Inert atmosphere;

Zhou, Meng; Schley, Nathan D.; Crabtree, Robert H.

Journal of the American Chemical Society, 2010 , vol. 132, # 36 p. 12550 - 12551 Title/Abstract

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With dihydrogen peroxide in water

T=69.84°C; 12 h;

Sasidharan, Manickam; Bhaumik, Asim

Journal of Molecular Catalysis A: Chemical, 2011 , vol. 338, # 1-2 p. 105 - 110 Title/Abstract

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With seteterlenium-doped TiO2; dihydrogen peroxide in water

T=24.84°C; 4.5 h; UV-irradiation; TimeReagent/catalyst;

Padmalatha, Patnam; Khatri, Praveen K.; Jain, Suman L.

Synlett, 2013 , vol. 24, # 11 art. no. ST-2013-B0027-L, p. 1405 - 1409 Title/Abstract

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With 2,2,5,7,8-pentamethylchroman-6-ol; oxygen; α,α'azodiizobutyramidine-dihydrochloride in aq. buffer T=30°C; pH=7.4; Kinetics; pH-valueSolventReagent/catalyst;

Amorati, Riccardo; Baschieri, Andrea; Morroni, Gloria; Gambino, Rossana; Valgimigli, Luca

Chemistry - A European Journal, 2016 , vol. 22, # 23 p. 7924 - 7934 Title/Abstract

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42 %Spectr.

With oxone in [(2)H6]acetone

3 h; Inert atmosphere; Hide Experimental Procedure

Yale University; Bloomfield, Aaron J.; Sheehan, Stafford W.; Collom, Samuel L.; Crabtree, Robert H.; Anastas, Paul T.

Patent: US2016/152648 A1, 2016 ; Location in patent: Paragraph 0209 ; Title/Abstract

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7:

A stock solution of KHSO5 was prepared in degassed D20 under N2. Catalyst (e.g., Co-dppe) was added to each reaction tube. The tubes were then evacuated under vacuum and refilled with N2 several times. 400 jtL of d5-ac- etone was added to each tube followed by the appropriate substrate. Reactions were initiated by the addition of 100 pL of KHSO5 stock solution. Reactions were monitored for 3 or 15 hrs depending on the substrate. The reactions were quenched by addition of a stock solution of d4-sodium trimethylsilyl propionate (NMR internal standard) and d5-dim- ethylsulfoxide (oxidant quench). The reactions stirred another 15 mm and then were filtered into NMR tubes. The reactions were quantified by NMR. (Control reactions were performed without catalyst and in each case the substrate conversion is >5percent)10209] For most of the substrates selective oxidation to a single product was observed. The catalyst system was able to oxidize unactivated alkanes to a single product but in low yield. Oxidation of 1 -butanol illustrates the difference the catalyst and simple cobalt salts. The catalyst selectively oxidizes butanol to

butyric acid whereas the CoOl) salts tested were highly unselective, affording several different products.

2

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Rx-ID: 18451 Find similar reactions

3

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Criegee

Angewandte Chemie, 1950 , vol. 62, p. 120 Full Text View citing articles Show Details

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Rx-ID: 36867 Find similar reactions

T=275°C; P=51485.6 Torr; Hydrogenation.an einen Nickel-ChromMolybdaen-Katalysator;

Du Pont de Nemours and Co.

Patent: US2772291 , 1953 ;

With cobalt

T=200°C; P=102971 Torr; Hydrogenation;

Du Pont de Nemours and Co.

Patent: US2772292 , 1953 ;

T=200°C; P=220652 Torr; Hydrogenation.an einem NickelMolybdaen-Katalysator;

Du Pont de Nemours and Co.

Patent: US2772293 , 1953 ;

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With hydrogen; Zn-Cu catalyst

T=270°C; P=760 Torr; 2 h;

Zhu, Yu-Lei; Xiang, Hong-Wei; Wu, Gui-Sheng; Bai, Liang; Li, Yong-Wang

Chemical Communications, 2002 , # 3 p. 254 - 255 Title/Abstract

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With Cu-CeO2-Al2O3; hydrogen

T=220°C; P=760.051 Torr; 1 h;

Yu, Yang; Guo, Yanglong; Zhan, Wangcheng; Guo, Yun; Wang, Yanqin; Wang, Yunsong; Zhang, Zhigang; Lu, Guanzhong

Journal of Molecular Catalysis A: Chemical, 2011 , vol. 337, # 1-2 p. 77 - 81 Title/Abstract

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With hydrogen

Yu, Yang; Guo, Yanglong; Zhan, Wangcheng; Guo, Yun; Wang, Yunsong; Lu, Guanzhong

T=220 - 600°C; P=760.051 Torr; 1 h; Reagent/catalystTime; Hide Experimental Procedure

Journal of Molecular Catalysis A: Chemical, 2014 , vol. 392, p. 1 - 7 Title/Abstract

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Gas-phase hydrogenation of MA to GBL was carried outin a tubular quartz fixed-bed reactor (inside diameter = 13 mm,length = 650 mm) at atmospheric pressure. 6 mL of catalyst (height = 45 mm) was packed in the constant temperature part of the reactor, and then 15 mL of quartz sand pre treated at 600 °C inair was loaded above the catalyst for the complete gasification ofthe raw material (20 wt.percent MA dissolved in GBL). Prior to the test, the as-prepared catalyst was activated by 60 mL min−1of 5 vol.percent H2/N2at 300 °C for 6 h (designated as the fresh catalyst). Then the temperature was lowered to 220 °C, and 27.5 N mL min−1 of pure H2 and 0.2 h−1 (liquid hourly space velocity, LHSV) of raw material, were fed into the reactor. The products

were sampled using the conical beakers cooled by an ice-bath at intervals of 1 h and analyzed by Perkin-Elmer Clarus 500 gas chromatograph equipped with a FID detector and a SE-54 capillary column (25 m × 0.32 mm × 1.0 m). The temperatures of the injector and detector were 220 °C, and the temperature of the column oven was kept at 100 °C for 1 min and then increased programmedly to 120 °C at the rate of 5C min−1.

With hydrogen

T=240 - 380°C; P=760.051 Torr; Gas phase; Hide Experimental Procedure

Yu, Yang; Zhan, Wangcheng; Guo, Yun; Lu, Guanzhong; Adjimi, Souheila; Guo, Yanglong

Journal of Molecular Catalysis A: Chemical, 2014 , vol. 395, p. 392 - 397 Title/Abstract

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2.2. Gas-phase hydrogenation of maleic anhydride

anhydrideGas-phase hydrogenation of maleic anhydride to -butyrolactone (GHMG) over Cu-CeO2-Al2O3catalyst was carriedout under atmospheric pressure in a quartz tubular fixed-bedreactor (13 mm I.D., 650 mm L.). In a bottom-up sequence, thereactor was packed with 1 mL of quartz sand pretreated at 600C inair, 6 mL of catalyst (height = 45 mm) and then 15 mL of pretreatedquartz sand for the complete gasification of raw material (MAdissolved in GBL, 20 wt.percent). The catalyst was reduced in situ by60 mL min−1of 5 vol.percent H2/N2at 380C for 7 h (designated as thefresh catalyst). Then the temperature was decreased until 240C,and the reactor was fed by 30 mL min−1of H2and 0.2 h−1ofLHSV of raw material. The products were collected in the conicalbeakers cooled by ice-bath at the interval of 1 h and analyzed byPerkin-Elmer Clarus 500 gas chromatograph equipped with a FIDdetector and a SE-54 capillary column (25 m × 0.32 mm × 1.0 m).Both temperatures of injector and detector were kept at 220C,and the temperature of column oven was kept at 100C for 1 minand then increased programmedly from 100C to 120C with aheating ramp of 5C min−1.

4

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Lukes; Pliml

Collection of Czechoslovak Chemical Communications, 1956 , vol. 21, p. 1602,1605 Full Text Show Details

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B

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5

A

T=25°C; Rate constant;

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Friess; Frankenburg

Journal of the American Chemical Society, 1952 , vol. 74, p. 2679 Full Text View citing articles Show Details

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6

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99%

With oxone; silica gel in dichloromethane

T=20°C; Baeyer-Villiger oxidation; 1 h;

Gonzalez-Nunez, Maria E.; Mello, Rossella; Olmos, Andrea; Asensio, Gregorio

Journal of Organic Chemistry, 2005 , vol. 70, # 26 p. 10879 - 10882 Title/Abstract

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99%

With acyltransferase from Mycobacterium smegmatis; dihydrogen peroxide; ethyl acetate in water

T=35°C; Baeyer-Villiger Ketone Oxidation; 2 h; Enzymatic reaction; Hide Experimental Procedure

Drozdz; Hanefeld; Szymaska; Jarzbski; Chrobok

Catalysis Communications, 2016 , vol. 81, p. 37 - 40 Title/Abstract

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2.2. General method for Baeyer-Villiger oxidation

General procedure: The ketone (0.25 mmol) and 0.5 ml of ethyl acetate (5.09 mmol)were introduced into a 25 ml round-bottom flask and the contents ofthe flask was shaken. Next, 4 mg of MsAcT was introduced, and 60percentaq. H2O2 (0.50 mmol) was added dropwise. The flask was sealed witha septum and mixed in a thermostated shaker (±0.5 °C) with orbital stirring at 250 rpm at 35 °C for 2 h to 5 days, depending on the reaction rate. Periodically, 10 μl of the sample diluted with 0.7 ml of dichloromethane was collected during the reaction to monitor the progress ofthe reaction utilising GC (Perkin Elmer Clarus 500 chromatographwith SUPELCOWAX™ 10 column (30 m × 0.2 mm × 0.2 μm) with ndecane as an external standard.The structure of the products were confirmed using GC–MS analysis(Agilent Gas Chromatograph 7890C equipped with a HP-5 MS column(30 m × 0.25 mm × 0.25 μm; MS Agilent 5975C, EI ionization 70 eV,and the results were compared to NIST/EPA/NIH Mass Spectral Library.

98%

With 2,2,2-trifluoroethanol; dihydrogen peroxide

24 h; Ambient temperature;

Matsumoto, Masakatsu; Kobayashi, Hisako

Heterocycles, 1986 , vol. 24, # 9 p. 2443 - 2447 Title/Abstract

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98%

With urea hydrogen peroxide adduct in decane; ethyl acetate

T=20°C; Baeyer-Villiger Ketone Oxidation; 2 h; Hide Experimental Procedure

Drozdz; Chrobok; Baj; Szymanska; Mrowiec-Bialon; Jarzebski

Applied Catalysis A: General, 2013 , vol. 467, p. 163 - 170 Title/Abstract

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General procedures for BVO with the biocatalysts and activity assays

General procedure: A solution of ketone (0.5 mmol) in ethyl acetate (1.5 mL) and n-decane (0.5 mmol, internal standard) was introduced into the 25-mL round-bottom ask, whereupon the biocatalyst (0.005–0.03 g) and UHP (or 60percent aqueous H2O2) 1 mmol were added. The flask was sealed with septum and mixed in a thermostat shaker (±0.5 °C) with orbital stirring of 180 rpm at 25–70 °C for 29–50 h, depending on the reaction rate. Periodically, during the reaction, 100 L of the samples diluted with ethyl acetate were collected to monitor progress of the reaction utilising GC. When the reaction was completed, the catalyst was filtered off and washed with ethyl acetate (3 × 5 mL). The filtrate was washed with 5 mL of a 10percent NaHCO3 solution in water, dried over anhydrous MgSO4 and concentrated in vacuum. The yields of the lactones after purication by column chromatography (with hexane:ethyl acetate ratio of 4:1 as an eluent) were in the range of 85–99percent.

97%

With bis-trimethylsilanyl peroxide; 1-hexyl-3-methylimidazolium chloroaluminate(III)

T=0 - 20°C; Baeyer-Villiger Ketone Oxidation; 1 h; Acidic conditionsInert atmosphere; Reagent/catalyst; Hide Experimental Procedure

Baj, Stefan; Slupska, Roksana; Chrobok, Anna; Drozdz, Agnieszka

Journal of Molecular Catalysis A: Chemical, 2013 , vol. 376, p. 120 - 126 Title/Abstract

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General procedure for cyclic ketones oxidation

General procedure: The ketone (1.5 mmol) and silyl peroxide (2.25 mmol for reactions with bis(silyl) peroxides and 3 mmol for reactions with t-butyl silyl peroxides) were added dropwise at 0 °C into the freshly synthesised [hmim][AlxCly] (2 mmol for reactions with bis(silyl) peroxides and 3 mmol for reactions with t-butyl silyl peroxides). Next, the solution was stirred under a nitrogen atmosphere at room temperature for 1–24 h (depending on the reaction rate). After this time, 5 ml of water was added to the post-reaction mixture, and the water phase was extracted with methylene chloride or diethyl ether (10× 5 ml). The organic layer was washed with 5 ml of water, dried over anhydrous MgSO4, filtered, concentrated in a vacuum (50 °C, 100 mbar) and purified by column chromatography (hexane:ethyl acetate (4:1)) when necessary. All products were characterised by comparison of their NMR spectra (see Supplementary data) with authentic samples [20].

96%

With dihydrogen peroxide; polystyrene-bound phenylselenic acid in dichloromethane

3 h; Ambient temperature;

Taylor, Richard T.; Flood, Lawrence A.

Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5160 - 5164 Title/Abstract

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96%

With Candida antarctica lipase B; 1-octanoic acid; dihydrogen peroxide in water

T=45°C; Baeyer-Villiger Ketone Oxidation; 1.5 h; Ionic liquidEnzymatic reaction; TimeSolvent;

Drozdz, Agnieszka; Erfurt, Karol; Bielas, Rafal; Chrobok, Anna

New Journal of Chemistry, 2015 , vol. 39, # 2 p. 1315 - 1321 Title/Abstract

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95%

With Sn[N(SO2C8F17)2]4; dihydrogen peroxide in 1,4-dioxane

Hao, Xiuhua; Yoshida, Akihiro; Nishikido, Joji

T=50°C; Baeyer-Villiger oxidation; 1 h;

Journal of Fluorine Chemistry, 2006 , vol. 127, # 2 p. 193 - 199 Title/Abstract

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92%

With 1-butyl-3-methylimidazolium hydrogen sulfate; urea-hydrogen peroxide

T=50°C; Baeyer-Villiger oxidation; 5 h;

Baj, Stefan; Chrobok, Anna

Synthetic Communications, 2008 , vol. 38, # 14 p. 2385 - 2391 Title/Abstract

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92%

With oxygen; benzaldehyde in 1,2-dichloro-ethane

T=20°C; Baeyer-Villiger Ketone Oxidation; 8 h; Hide Experimental Procedure

Zhou, Weiyou; Chen, Yong; Qian, Junfeng; Sun, Fu’an; He, Mingyang; Chen, Qun

Catalysis Letters, 2016 , vol. 146, # 10 p. 2157 - 2164 Title/Abstract

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2.3 Catalytic B-V Oxidation

General procedure: The catalytic oxidation of ketone was carried out in a roundbottomflask of 25 mL volume equipped with magnetic stirrer.In the typical experiment, the flask was charged withsubstrate (2 mmol), CuPcTs-Zn2Al-LDH (8.0 mg), dichloroethane(10 mL), benzaldehyde (5 mmol), naphthalene(inert internal standard, 0.3 mmol) and then the mixture wasstirred at room temperature. Dioxygen was bubbled throughthe solution (10 mL min−1). We sampled during the reactionand the products were analyzed by GC-FID and GC-MSanalysis.

91%

With bis-trimethylsilanyl peroxide; 1-(n-butyl)-3-methylimidazolium triflate

T=25°C; Baeyer-Villiger oxidation; 1 h; Ionic liquidInert atmosphere;

Baj, Stefan; Chrobok, Anna; Slupska, Roksana

Green Chemistry, 2009 , vol. 11, # 2 p. 279 - 282 Title/Abstract

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88%

With dihydrogen peroxide in water

T=50°C; Baeyer-Villiger Ketone Oxidation; 3 h; Catalytic behavior; Reagent/catalyst; Hide Experimental Procedure

Li, Xinzhong; Cao, Rong; Lin, Qi

Catalysis Communications, 2015 , vol. 63, p. 79 - 83 Title/Abstract

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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 under 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.

85%

With dihydrogen peroxide; 3,5-bis(perfluorooctyl)phenyl butylselenide in Hexafluorobenzene; 2,2,2-trifluoroethanol

T=20°C; 2 h;

Ten Brink, Gerd-Jan; Vis, J.Martijn; Arends, Isabel W.C.E; Sheldon, Roger A

Tetrahedron, 2002 , vol. 58, # 20 p. 3977 - 3983 Title/Abstract

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85%

With urea hydrogen peroxide adduct; potassium hydrogencarbonate; benzonitrile in 2,2,2-trifluoroethanol

T=50°C; Baeyer-Villiger Ketone Oxidation; 18 h; Inert atmosphereSealed tube; Hide Experimental Procedure

Bradley, Tyne D.; Dragan, Andrei; Tomkinson, Nicholas C.O.

Tetrahedron, 2015 , vol. 71, # 42 p. 8155 - 8161 Title/Abstract

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13:General Baeyer-Villiger procedure

General procedure: To a flame dried crimp top vial under argon, KHCO3 (80mg, 0.8mmol, 0.2equiv) was weighed, followed by urea hydrogen peroxide (564mg, 24mmol, 6.0equiv). The ketone (4.0mmol, 1.0equiv) was added at this stage if it was a solid. The vial was then sealed and evacuated, followed by backfilling with argon (repeated three times). Afterward, the solvent (8.0mL), benzonitrile (2.48mL, 24mmol, 6.0equiv) and, if it was a liquid, the ketone (4.0mmol, 1.0equiv), were added via syringe. The reaction was allowed to run for the specified time at 50°C, after which it was cooled down to room temperature. The pressure was released with a needle, then the vial was opened. The mixture was diluted with CH2Cl2 (40mL) and water (20mL). The layers were separated and the resulting aqueous solution was extracted with CH2Cl2 (2×40mL). The combined organic layers were dried (MgSO4), concentrated in vacuo, and the crude product was subjected to flash chromatography on silica gel (5:1 petroleum ether:EtOAc) to afford the corresponding product(s).

62%

With [γ-W10SiO36(PhPO)2][TBA]4; dihydrogen peroxide in acetonitrile

T=90 - 120°C; 0.833333 h; microwave irradiation;

Carraro, Mauro; Sandei, Luca; Sartorel, Andrea; Scorrano, Gianfranco; Bonchio, Marcella

Organic Letters, 2006 , vol. 8, # 17 p. 3671 - 3674 Title/Abstract

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54%

With ReCl2{N2C(O)Ph}(pyrazole)2(PPh3); dihydrogen peroxide in water; 1,2-dichloro-ethane

T=70°C; Baeyer-Villiger Ketone Oxidation; 30 h; Hide Experimental Procedure

Alegria, Elisabete C.B.A.; Martins, Luisa M.D.R.S.; Kirillova, Marina V.; Pombeiro, Armando J.L.

Applied Catalysis A: General, 2012 , vol. 443-444, p. 27 - 32 Title/Abstract

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General procedure: In typical conditions, Re catalysts were used as stock solutions (for this, 10.0 mg of the compound 1–10 were dissolved in 2.00 mL of 1,2-dichloroethane, 1,2 DCE). The required amount of this stock solution for the desired oxidant/catalyst molar ratio (1000:1) was transferred to a second flask containing 3.00 mL of 1,2-dichloroethane. 1.7 mmol of H2O2 as a 30percent aqueous solution (102 μL) and 1.7 mmol of substrate were then added, and the reaction solution was stirred for 6 h at the desired temperature (typically 70 °C) and normal pressure (dinitrogen atmosphere). Then, 120 μL of cycloheptanone (internal standard) and 10.00 mL of diethyl ether (to extract the substrate and the organic products from the reaction mixture) were added. The obtained mixture was stirred during 10 min and then a sample (1 μL) was taken from the organic phase and analysed by GC using the internal standard method. Blank tests indicate that no oxidation takes place in the absence of the Re catalyst or the oxidant.

48%

With dihydrogen peroxide in acetonitrile

T=20°C; 16 h;

Starkl Renar; Pear; Iskra

Organic and Biomolecular Chemistry, 2015 , vol. 13, # 36 p. 9369 - 9372 Title/Abstract

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36%

With [ReO3(η2-hydrotris(pyrazol-1-yl)-methane)(1,3,5-triaza-7phosphaadamantane)][ReO4]; dihydrogen peroxide in 1,2-dichloroethane

T=70°C; Baeyer-Villiger Ketone Oxidation; 6 h; Inert atmosphere; Catalytic behavior; Reagent/catalystConcentration;

Martins, Luisa M. D. R. S.; Alegria, Elisabete C. B. A.; Smolenski, Piotr; Kuznetsov, Maxim L.; Pombeiro, Armando J. L.

Inorganic Chemistry, 2013 , vol. 52, # 8 p. 4534 - 4546 Title/Abstract

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34.2%

With D-(+)-glucose in aq. buffer T=15°C; 16 h; Hide Experimental Procedure

Bisagni, Serena; Smus, Justyna; Chvez, Georgina; Hatti-Kaul, Rajni; Mamo, Gashaw

Journal of Molecular Catalysis B: Enzymatic, 2014 , vol. 109, p. 161 - 169 Title/Abstract

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2.5 Biotransformations using whole cells and crude cell extract

General procedure: Whole-cell biotransformations were performed using both growing and resting cells. For growing cells, 2 ml TB medium in a 15 ml Falcon tube was inoculated with a pre-culture of E. coli BL21-CodonPlus(DE3)-RP cells containing the recombinant plasmid with the BVMO gene. The cells were grown for 3 h at 30 °C and with shaking at 150 rpm. Immediately after adding IPTG, the biotransformation reaction was initiated by adding the substrate to a final concentration of 5 mM. To boost the regeneration of NADPH, glucose (25 mM) was also added at the moment of induction. Biotransformations were carried out for 16 h at 15 °C and at a shake rate of 150 rpm. The level of conversion was measured by comparing E. coli BL21-CodonPlus(DE3)RP expressing BVMO3 with cells from the same E. coli strain carrying pET-22b(+) without the BVMO3 gene, that served also as a blank for side reactions.

With Perbenzoic acid; chloroform

Friess; Frankenburg

Journal of the American Chemical Society, 1952 , vol. 74, p. 2679 Full Text View citing articles Show Details

83 % Chromat.

With oxygen; benzaldehyde; iron(III) oxide in benzene

P=760 Torr; 17 h; Ambient temperature;

Murahashi, Shun-Ichi; Oda, Yoshiaki; Naota, Takeshi

Tetrahedron Letters, 1992 , vol. 33, # 49 p. 7557 - 7560 Title/Abstract

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With perfluoro(methylcyclohexane); water; dihydrogen peroxide; Sn[N(SO2C8F17)2]4 in 1,4-dioxane

T=50°C; Baeyer-Villiger oxidation; 1 h;

Hao, Xiuhua; Yamazaki, Osamu; Yoshida, Akihiro; Nishikido, Joji

Tetrahedron Letters, 2003 , vol. 44, # 27 p. 4977 - 4980 Title/Abstract

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64 % Chromat.

With dihydrogen peroxide; fluorous reverse-phase silica gelSn[N(SO2C8F17)2]4 in water

T=25°C; Baeyer-Villiger reaction; 1.5 h;

Yamazaki, Osamu; Hao, Xiuhua; Yoshida, Akihiro; Nishikido, Joji

Tetrahedron Letters, 2003 , vol. 44, # 49 p. 8791 - 8795 Title/Abstract

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98 % Chromat.

With dihydrogen peroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate; methyltrioxorhenium(VII) in water

T=20°C; Baeyer-Villiger oxidation; 1 h;

Bernini, Roberta; Coratti, Antonietta; Fabrizi, Giancarlo; Goggiamani, Antonella

Tetrahedron Letters, 2003 , vol. 44, # 50 p. 8991 - 8994 Title/Abstract

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With peracetic acid; tungsten(VI) oxide in acetonitrile

T=60°C; Baeyer-Villiger oxidation; 12 h;

Koo, Dong Hyun; Kim, Min; Chang, Sukbok

Organic Letters, 2005 , vol. 7, # 22 p. 5015 - 5018 Title/Abstract

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With oxone; oxone; silica gel in carbon dioxide

T=40°C; Baeyer-Villiger oxidation; P=187515 Torr;

Gonzalez-Nunez, Maria E.; Mello, Rossella; Olmos, Andrea; Asensio, Gregorio

Journal of Organic Chemistry, 2006 , vol. 71, # 17 p. 6432 - 6436 Title/Abstract

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With dihydrogen peroxide; γ-Keggin-type silicodecatungstate dimer in nitromethane; water

T=59.85°C; Baeyer-Villiger oxidation; 0.0833333 h;

Yoshida, Akihiro; Yoshimura, Masayuki; Uehara, Kazuhiro; Hikichi, Shiro; Mizuno, Noritaka

Angewandte Chemie - International Edition, 2006 , vol. 45, # 12 p. 1956 - 1960 Title/Abstract

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With dibutyl ether; bis[3,5-bis(trifluoromethyl)diphenyl] diselenide in 2,2,2-trifluoroethanol

T=20°C; Baeyer-Villiger oxidation; 1 h;

Ten Brink; Vis; Arends; Sheldon

Journal of Organic Chemistry, 2001 , vol. 66, # 7 p. 2429 - 2433 Title/Abstract

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With [SiO2]-CH2CH2CO3H in supercritical carbon dioxide

T=40°C; Baeyer-Villiger oxidation; P=187519 Torr; Flow conditions;

Mello, Rossella; Olmos, Andrea; Parra-Carbonell, Javier; Gonzalez-Nunez, Maria Elena; Asensio, Gregorio

Green Chemistry, 2009 , vol. 11, # 7 p. 994 - 999 Title/Abstract

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100 %Chromat.

With dihydrogen peroxide in 1,1,1,3',3',3'-hexafluoropropanol; water

T=50°C; Baeyer-Villiger oxidation; 1.5 h;

Piscopo, Calogero G.; Loebbecke, Stefan; Maggi, Raimondo; Sartori, Giovanni

Advanced Synthesis and Catalysis, 2010 , vol. 352, # 10 p. 1625 - 1629 Title/Abstract

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With Candida antarctica Lipase type B; urea hydrogen peroxide adduct in ethyl acetate

Gonzlez-Martnez, Daniel; Rodrguez-Mata, Mara; Mndez-Snchez, Daniel; Gotor, Vicente; Gotor-Fernndez, Vicente

Journal of Molecular Catalysis B: Enzymatic, 2015 , vol. 114, p. 31 - 36

T=30°C; Baeyer-Villiger Ketone Oxidation; 24 h; Enzymatic reaction; Hide Experimental Procedure

2.7 General procedure for the chemoenzymatic synthesis of lactones 2a–l using CAL-B, UHP and EtOAc

General procedure: Over a solution of the corresponding cyclobutanone 1a–l (0.25 mmol) in EtOAc (379 μL, 30.0 mmol), complex urea-hydrogen peroxide (UHP, 35 mg, 0.38 mmol) and CAL-B (12.5 mg) were added. The suspension was shaken for 20 h at 30 °C and 250 rpm, then an aliquot was analyzed by GC. The reaction was left shaken until complete conversion was reached, then water was added (2 mL) and the enzyme filtered off. The solution was extracted with EtOAc (3× 5 mL) and the organic phases combined and washed with water (2× 5 mL) and brine (5 mL). The resulting organic phase was dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure to obtain the corresponding lactones 2a–l (51–99percent isolated yield).

For fluorinated lactone 2k a column chromatography on silica gel (30percent EtOAc/hexane) was necessary, as the reaction did not lead to complete conversion.

With dihydrogen peroxide in 1,2-dichloro-ethane

T=90°C; Baeyer-Villiger Ketone Oxidation; 2 h; Hide Experimental Procedure

With alpha-D-glucopyranose; glucose dehydrogenase (GDH105); Baeyere-Villiger monooxygenase P1-D08; oxygen in methanol; aq. phosphate buffer

T=30°C; Baeyer-Villiger Ketone Oxidation; pH=9; 24 h; Enzymatic reaction; Reagent/catalystpH-valueTemperatureSolvent; Hide Experimental Procedure

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Rodríguez-Mata, María; Lavandera, Iván; Gotor-Fernández, Vicente; Gotor, Vicente; García-Cerrada, Susana; Mendiola, Javier; de Frutos, Óscar; Collado, Iván

Tetrahedron, 2016 , vol. 72, # 46 p. 7268 - 7275 Title/Abstract

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4.4.1. General procedure for the BVMO-catalyzed oxidation of prochiralcyclobutanones 1a-j, m-v.

General procedure: In a typical experiment carried out in 1.5 mL tubes (total volume of 500 μL), the substrate 1a-j, m-v (10 mM) was dissolved in methanol (5 μL, 1percent v/v) and KPi buffer (100 mM, pH 9.0, 482 μL), containing glucose (20 mM), glucose dehydrogenase (GDH-105, 10 U, from stock solution of 1.275 U/μL), NADPH (0.2 mM, from a 20 mM stock solution) and the corresponding Baeyere-Villiger monooxygenase (2 mg). The mixture was shaken at 250 rpm at 30 °C for 24 h. The reaction was stopped by extracting with diethyl ether (2x400 μL) and centrifugedat 13,000 rpm in order to separate both phases and pellet the suspended protein. The organic phases were combined, dried over anhydrous sodium sulfate and analyzed by GC in order to determine the conversion values. Then, the solvent in GC samples was evaporated with a continuous flow of nitrogen, the residue redissolved in a mixture of hexane:ethanol 90:10 and the new sample filtered and analyzed by HPLC, leading to the measurement of the enantiomeric excess of the lactones. Control experiments in the absence of enzyme were performed for all substrates, not observing any reaction product after similar periods of time (Tables S1-S19).

7

Zheng, Weiguo; Tan, Rong; Luo, Xuanfeng; Xing, Chen; Yin, Donghong

Catalysis Letters, 2016 , vol. 146, # 2 p. 281 - 290 Title/Abstract

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2.3 B–V Oxidation of Ketones with H2O2

General procedure: SnO2/GO nanocomposites (0.05 g) and ketones (1.0 mmol) were mixed in 1,2-dichloroethane (15 mL) under vigorously stirring. H2O2 (30 wtpercent, 2.0 mmol) was then added dropwise at 90 °C. The reaction progress was monitored by GC. After the reaction, catalyst was separated by centrifugation. The liquid reaction mixture was extracted by ethyl ether and then quantitatively analyzed by a 6890 N gas chromatograph (Agilent Co.) equipped with the capillary column (HP19091G-B213, 30 m x 0.32 mm x 0.25 μm). The recovered catalyst was washed with ethanol and distilled water repeatedly, and dried at 40 °C overnight for reused.

Title/Abstract

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98%

With phosphoric acid tributyl ester

T=119.84°C; P=9375.94 Torr; 8 h; Autoclave; Catalytic behavior; Reagent/catalyst;

Li, Xian; Cui, Yuanyuan; Yang, Xinli; Dai, Wei-Lin; Fan, Kangnian

Applied Catalysis A: General, 2013 , vol. 458, p. 63 - 70 Title/Abstract

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98%

With Cu–Al hydrotalcite in 1,4-dioxane

T=220°C; P=12001.2 Torr; 0.045 h;

Aellig, Christof; Jenny, Florian; Scholz, David; Wolf, Patrick; Giovinazzo, Isabella; Kollhoff, Fabian; Hermans, Ive

Catalysis Science and Technology, 2014 , vol. 4, # 8 p. 2326 - 2331 Title/Abstract

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97%

With 4-hydroxy-TEMPO benzoate; sodium bromide in dichloromethane; water

NaHCO3-buffered at pH 8.6; electrolysis;

Inokuchi, Tsutomu; Matsumoto, Sigeaki; Torii, Sigeru

Journal of Organic Chemistry, 1991 , vol. 56, # 7 p. 2416 - 2421 Title/Abstract

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97%

With tris(cetyl)pyridinium 12-tungstophosphate; dihydrogen peroxide in tert-butyl alcohol

24 h; Heating;

Ishii, Yasutaka; Yamawaki, Kazumasa; Ura, Toshikazu; Yamada, Hiroshi; Yoshida, Tsutomu; Ogawa, Masaya

Journal of Organic Chemistry, 1988 , vol. 53, # 15 p. 3587 - 3593 Title/Abstract

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97%

With hydrotalcite-supported copper nanoparticles in 1,3,5-

Mikami, Yusuke; Ebata, Kaori; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

trimethyl-benzene

T=150°C; 3 h; Inert atmosphere;

Heterocycles, 2010 , vol. 80, # 2 p. 855 - 861 Title/Abstract

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97%

With sodium hypochlorite; sodium hydrogencarbonate; potassium bromide in dichloromethane

T=0°C; 0.5 h; chemoselective reaction;

Tucker-Schwartz, Alexander K.; Garrell, Robin L.

Chemistry - A European Journal, 2010 , vol. 16, # 42 p. 12718 - 12726 Title/Abstract

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97.9%

With Cu—ZnO—Al2O3—ZrO3 catalyst T=240°C; Inert atmosphereFlow reactor; Hide Experimental Procedure

Lee, Han Won; Yang, Young Lyeol; Kim, So Young; Shin, Yong Uk; Chang, Jin Sook; Um, Hye Won; Goh, Young Hyoung; Jhon, Sung Hoo

Patent: US2014/296466 A1, 2014 ; Location in patent: Paragraph 0264; 0265 ; Title/Abstract

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16.2:16-2) Production of Gamma-Butyrolactone

The carrier gas, nitrogen, was flowed downward from the upper part of the fixed-bed flow reactor having the Cu—ZnO—Al2O3—ZrO3 catalyst layer at a flow rate of 30 ml/min under atmospheric pressure. 1,4-butanediol was supplied together with the nitrogen gas, vaporized in the vaporizing layer and supplied to the catalyst layer. Herein, the temperature of the vaporizing layer and the catalyst layer was 240° C. Upon the increase of LHSV (liquid hourly space velocity) to 0.5 h−1 of 1,4-butanediol, the maximum yield of gamma-butyrolactone were 97.9percent.

96%

With (CH3)5C5*Ir(-OCH2C(C6H5)2NH-) in acetone

T=20°C; 20 h;

Suzuki, Takeyuki; Morita, Kenji; Tsuchida, Mika; Hiroi, Kunio

Organic letters, 2002 , vol. 4, # 14 p. 2361 - 2363 Title/Abstract

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96%

With potassium hydroxide; PS-resin; potassium hexacyanoferrate(III); 4-(benzyloxycarbonyl)-2,2,6,6tetramethylpiperidine-1-oxyl in water; toluene

T=20°C; 4 h;

Yoshitomo, Kashiwagi; Chiba, Shinya; Anzai, Jun-ichi

New Journal of Chemistry, 2003 , vol. 27, # 11 p. 1545 - 1549 Title/Abstract

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96%

With oxygen in toluene

T=80°C; 2 h;

Mitsudome, Takato; Noujima, Akifumi; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Green Chemistry, 2009 , vol. 11, # 6 p. 793 - 797 Title/Abstract

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96%

With C42H36ClIrO2P2; caesium carbonate in para-xylene

12 h; Inert atmosphereReflux;

Musa, Sanaa; Shaposhnikov, Irina; Cohen, Shmuel; Gelman, Dmitri

Angewandte Chemie - International Edition, 2011 , vol. 50, # 15 p. 3533 - 3537 Title/Abstract

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95%

With sodium bromite; 4-benzoxy-2,2,6,6-tetramethylpiperidine-Noxyl; sodium hydrogencarbonate in dichloromethane; water

3 h; Ambient temperature;

Inokuchi, Tsutomo; Matsumoto, Sigeaki; Nishiyama, Tokio; Torii, Sigeru

Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 462 - 466 Title/Abstract

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95%

With (1,10-phenanthroline)H2CrOCl5 in dichloromethane

T=25°C; 8 h;

Chakraborty, T. K.; Chandrasekaran, S.

Tetrahedron Letters, 1980 , vol. 21, p. 1583 - 1586 Title/Abstract

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95%

With (bipyH2)-CrOCl5 in dichloromethane

4 h; Ambient temperature;

Chakraborty, T. K.; Bhushan, Vidya; Chandrasekaran, S.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983 , vol. 22, # 1 p. 9 - 11 Title/Abstract

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95%

With (bipyH2)-CrOCl5 in dichloromethane

4 h; Ambient temperatureother oxidant, other substrate;

Chakraborty, T. K.; Bhushan, Vidya; Chandrasekaran, S.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983 , vol. 22, # 1 p. 9 - 11 Title/Abstract

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95%

With aluminum oxide; potassium permanganate; copper(II) sulfate

T=20°C; 14 h;

Shaabani, Ahmad; Lee, Donald G.

Tetrahedron Letters, 2001 , vol. 42, # 34 p. 5833 - 5836 Title/Abstract

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95%

With horse liver alcohol dehydrogenase; oxygen; catalase; 7(trifluoromethyl)-1,10-ethyleneisoalloxazinium chloride in aq. phosphate buffer

T=20°C; pH=8; 6 h; Enzymatic reaction; Catalytic behavior; Reagent/catalyst;

Zhu, Chenjie; Li, Qing; Pu, Lingling; Tan, Zhuotao; Guo, Kai; Ying, Hanjie; Ouyang, Pingkai

ACS Catalysis, 2016 , vol. 6, # 8 p. 4989 - 4994 Title/Abstract

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94%

With aluminum oxyhydroxide; ruthenium in toluene

T=110°C; 32 h;

Kim, Won-Hee; Park, In Soo; Park, Jaiwook

Organic Letters, 2006 , vol. 8, # 12 p. 2543 - 2545

Title/Abstract

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92%

With sodium bromite in water; acetic acid

10 h; Ambient temperature;

Kageyama, Toshifumi; Kawahara, Shuji; Kitamura, Kohji; Ueno, Yoshio; Okawara, Makoto

Chemistry Letters, 1983 , p. 1097 - 1100 Title/Abstract

Full Text Show Details

92%

With aluminum oxide; sodium bromite in dichloromethane

Ambient temperature;

Morimoto, Takashi; Hirano, Masao; Iwasaki, Keiko; Ishikawa, Takashi

Chemistry Letters, 1994 , # 1 p. 53 - 54 Title/Abstract

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92%

OTSUKA KAGAKU KABUSHIKI KAISHA

Patent: EP1178026 A1, 2002 ; Location in patent: Page 11 ; Title/Abstract

Full Text Show Details

91.1%

With oxygen; K-L zeolite; palladium in various solvent(s) T=83.9 - 117.9°C; P=757.6 Torr; 24 h; other supporting zeolites, other solvents, other temperatures;

Baba; Kameta; Nishiyama; Tsuruya; Masai

Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 1 p. 255 - 257 Title/Abstract

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91%

With caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene in 1,3,5-trimethyl-benzene

T=157°C; 24 h;

Oded, Kobi; Musa, Sanaa; Gelman, Dmitri; Blum, Jochanan

Catalysis Communications, 2012 , vol. 20, p. 68 - 70 Title/Abstract

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91%

With [{Cu2(5-phenyl-2,8-bis(6′-bipyridinyl)-1,9,10-anthyridine)-(μClO4)2}(PF6)2]; dihydrogen peroxide; sodium acetate in water

T=70°C; 12 h;

Huang, Da-Wei; Liu, Yi-Hung; Peng, Shie-Ming; Liu, Shiuh-Tzung

Organometallics, 2016 , vol. 35, # 2 p. 151 - 158 Title/Abstract

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90%

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor in tert-butyl methyl ether

T=30°C; pH=5.5; 12 h; Enzymatic reaction;

Díaz-Rodríguez, Alba; Martínez-Montero, Lía; Lavandera, Iván; Gotor, Vicente; Gotor-Fernández, Vicente

Advanced Synthesis and Catalysis, 2014 , vol. 356, # 10 p. 2321 - 2329 Title/Abstract

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89%

With N-iodo-succinimide; silver(I) acetate in benzene

7.5 h; Heating;

Beebe, Thomas R.; Adkins, Rick; Baldridge, Ruth; Hensley, Vivian; McMillen, Doug; et al.

Journal of Organic Chemistry, 1987 , vol. 52, # 24 p. 5472 - 5474 Title/Abstract

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89%

With N-iodo-succinimide; silver(I) acetate in benzene

7.5 h; Heatingvar. time of reaction' var. diols; MechanismProduct distribution;

Beebe, Thomas R.; Adkins, Rick; Baldridge, Ruth; Hensley, Vivian; McMillen, Doug; et al.

Journal of Organic Chemistry, 1987 , vol. 52, # 24 p. 5472 - 5474 Title/Abstract

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89%

Electrolysis;

OTSUKA KAGAKU KABUSHIKI KAISHA

Patent: EP1178026 A1, 2002 ; Location in patent: Page 14 ; Title/Abstract

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88%

With N-chloro-succinimide in dichloromethane

T=20°C; 5 h;

Kondo; Kawasoe; Kunisada; Yuki

Synthetic Communications, 1995 , vol. 25, # 5 p. 719 - 724 Title/Abstract

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88%

With N-chloro-succinimide in dichloromethane

T=20°C; 5 h; var. solvents, other α,ω-diol; Product distribution;

Kondo; Kawasoe; Kunisada; Yuki

Synthetic Communications, 1995 , vol. 25, # 5 p. 719 - 724 Title/Abstract

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87%

With trichloromelamine in dichloromethane

12 h; Ambient temperature;

Kondo, Shuji; Ohira, Mari; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo

Journal of Organic Chemistry, 1993 , vol. 58, # 18 p. 5003 - 5004 Title/Abstract

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86%

With peracetic acid; sodium bromide in ethyl acetate

T=39.9°C; 2 h;

Morimoto, Takashi; Hirano, Masao; Hamaguchi, Takayoshi; Shimoyama, Masahide; Zhuang, Xiumin

Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 3 p. 703 - 706 Title/Abstract

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86%

With C34H37N4O6Ru2(1+)*Cl(1-); potassium hydoxide in toluene

T=70°C; 6 h; Schlenk techniqueInert atmosphere;

Dutta, Indranil; Sarbajna, Abir; Pandey, Pragati; Rahaman, S. M. Wahidur; Singh, Kuldeep; Bera, Jitendra K.

Organometallics, 2016 , vol. 35, # 10 p. 1505 - 1513 Title/Abstract

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85%

With RuH3(Ph3P)3 in benzene

T=40°C; 24 h;

Lin, Yingrui; Zhu, Xianchao; Zhou, Yuefen

Journal of Organometallic Chemistry, 1992 , vol. 429, # 2 p. 269 - 274 Title/Abstract

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85%

With RuH4(iPr3P)2 in benzene

T=40°C; 24 h; other diols, var. transition metal polyhydrides and reaction conditions; Mechanism;

Lin, Yingrui; Zhu, Xianchao; Zhou, Yuefen

Journal of Organometallic Chemistry, 1992 , vol. 429, # 2 p. 269 - 274 Title/Abstract

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85%

With (PNPiPr)Fe(H)(CO) in toluene

T=120°C; 20 h; Schlenk techniqueInert atmosphere;

Chakraborty, Sumit; Lagaditis, Paraskevi O.; Förster, Moritz; Bielinski, Elizabeth A.; Hazari, Nilay; Holthausen, Max C.; Jones, William D.; Schneider, Sven

ACS Catalysis, 2014 , vol. 4, # 11 p. 3994 - 4003 Title/Abstract

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85%

With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate in acetonitrile

T=22°C; 6 h; Reagent/catalyst;

Xie, Xiaomin; Stahl, Shannon S.

Journal of the American Chemical Society, 2015 , vol. 137, # 11 p. 3767 - 3770 Title/Abstract

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84%

With silica gel; sodium hydrogencarbonate; sodium bromide; 4hydroxy-TEMPO benzoate in water

T=20°C; Electrochemical reaction;

Tanaka, Hideo; Kawakami, Yusuke; Goto, Kentaro; Kuroboshi, Manabu

Tetrahedron Letters, 2001 , vol. 42, # 3 p. 445 - 448 Title/Abstract

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84%

With Knolker's complex; acetone

T=60°C; Oppenauer-type oxidation; 24 h; Inert atmosphere;

Coleman, Michael G.; Brown, Alec N.; Bolton, Brett A.; Guan, Hairong

Advanced Synthesis and Catalysis, 2010 , vol. 352, # 6 p. 967 - 970 Title/Abstract

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82%

With 1,1'-bis-(diphenylphosphino)ferrocene; [(η6-pMeC6H4Pri)2Ru2Cl2(μ-Cl)2]; potassium carbonate; 4- methyl-2pentanone

Oppenauer Oxidation; 0.5 h; RefluxSchlenk techniqueInert atmosphere;

Nicklaus, Céline M.; Phua, Pim Huat; Buntara, Teddy; Noel, Sebastien; Heeres, Hero J.; De Vries, Johannes G.

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 14-15 p. 2839 - 2844 Title/Abstract

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81%

With triethylamine; 1-Phenylbut-1-en-3-one; Ru2Cl4((-)-diop)3

T=190°C; 5 h;

Ishii, Youichi; Osakada, Kohtaro; Ikariya, Takao; Saburi, Masahiko; Yoshikawa, Sadao

Chemistry Letters, 1982 , p. 1179 - 1182 Title/Abstract

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81%

With 1-oxo-4-methoxy-2,2,6,6-tetramethylpiperidinium chloride in dichloromethane

T=25°C; 0.166667 h;

Miyazawa, Takeo; Endo, Takeshi

Journal of Organic Chemistry, 1985 , vol. 50, # 20 p. 3930 - 3931 Title/Abstract

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81%

With oxygen; Pd on Na-ZSM-5 zeolite in various solvent(s) T=117.9°C; 24 h;

Baba, T.; Kameta, K.; Nishiyama, S.; Tsuruya, S.; Masai, M.

Journal of the Chemical Society, Chemical Communications, 1989 , # 15 p. 1072 - 1073 Title/Abstract

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79%

With allyl methyl carbonate; dihydridotetrakis(triphenylphosphine)ruthenium(II) in toluene

3.5 h; Heating;

Minami, Ichiro; Tsuji, Jiro

Tetrahedron, 1987 , vol. 43, # 17 p. 3903 - 3916 Title/Abstract

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78%

With sodium bromate; hydrogen bromide in tetrachloromethane

T=37°C; 5 h;

Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Yamasaki, Hiromochi; Fujisaki, Shizuo

Bulletin of the Chemical Society of Japan, 1986 , vol. 59, # 3 p. 747 - 750 Title/Abstract

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76%

With pyridine; trichloroisocyanuric acid in dichloromethane

5 h; Heating;

Hiegel, Gene A.; Gilley, Cynthia B.

Synthetic Communications, 2003 , vol. 33, # 12 p. 2003 - 2009 Title/Abstract

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76%

With platinum in neat (no solvent) T=180°C; P=760.051 Torr; 36 h; Inert atmosphere;

Touchy, Abeda Sultana; Shimizu, Ken-Ichi

RSC Advances, 2015 , vol. 5, # 37 p. 29072 - 29075 Title/Abstract

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75%

Stage #1: With 1-(4-hydroxy-3,5-dimethoxy-phenyl)ethanone; horseliver alcohol dehydrogenase; NAD in aq. buffer T=30°C; 0.0833333 h; Enzymatic reaction; Stage #2: With laccase from Myceliophthora thermophila in aq. buffer pH=7; 22 h;

Koenst, Paul; Kara, Selin; Kochius, Svenja; Holtmann, Dirk; Arends, Isabel W. C. E.; Ludwig, Roland; Hollmann, Frank

ChemCatChem, 2013 , vol. 5, # 10 p. 3027 - 3032 Title/Abstract

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72%

With manganese(IV) oxide in chloroform

24 h; Heating;

Phillips, David J.; Graham, Andrew E.

Synlett, 2008 , # 5 p. 649 - 652 Title/Abstract

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72%

With manganese(IV) oxide in chloroform

Reflux;

Bagley, Mark C.; Lin, Zhifan; Phillips, David J.; Graham, Andrew E.

Tetrahedron Letters, 2009 , vol. 50, # 49 p. 6823 - 6825 Title/Abstract

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71%

With sodium hypochlorite; 2,2,6,6-tetramethyl-4(3',3',4',4',5',5',6',6',6'-nonafluorohexyl)-(3'',3'',4'',4'',5'',5'',6'',6'',6''nonafluorohexan)amidepiperidin-1-oxyl; potassium bromide in dichloromethane

T=0°C; 1 h; aq. buffer;

Dobbs, Adrian P.; Penny, Mark J.; Jones, Peter

Tetrahedron Letters, 2008 , vol. 49, # 49 p. 6955 - 6958 Title/Abstract

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71%

With sodium hypochlorite; 2,2,6,6-tetramethyl-4(3',3',4',4',5',5',6',6',6'-nonafluorohexyl)-(3'',3'',4'',4'',5'',5'',6'',6'',6''nonafluorohexan)amidepiperidin-1-oxyl; sodium hydrogencarbonate; potassium bromide in dichloromethane

T=0 - 20°C; 1.33333 h; aq. buffer;

Dobbs, Adrian P.; Jones, Peter; Penny, Mark J.; Rigby, Stephen E.

Tetrahedron, 2009 , vol. 65, # 27 p. 5271 - 5277 Title/Abstract

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71%

With [RuCl2(p-cymene)(iPr2-imy)]; potassium hydoxide; PCy3 in 1,3,5-trimethyl-benzene

T=163°C; 18 h; Inert atmosphere;

Solvhoj, Amanda; Madsen, Robert

Organometallics, 2011 , vol. 30, # 21 p. 6044 - 6048 Title/Abstract

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70%

With potassium dichromate in N,N-dimethyl-formamide

20 h; Ambient temperature;

Kim, Kwan Soo; Szarek, Walter A.

Carbohydrate Research, 1982 , vol. 104, p. 328 - 333 Title/Abstract

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62%

With sodium bromate; sodium hydrogensulfite in acetonitrile

2 h; Heating;

Takase, Kiyoshi; Masuda, Haruyoshi; Kai, Osamu; Nishiyama, Yutaka; Sakaguchi, Satoshi; Ishii, Yasutaka

Chemistry Letters, 1995 , # 10 p. 871 - 872 Title/Abstract

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60%

With disodium hydrogenphosphate; benzyltrimethylammonium tribromide in tetrachloromethane; water

T=70°C; 5.5 h;

Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo

Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 8 p. 2585 - 2588 Title/Abstract

Full Text Show Details

59%

With N-oxyl-immobilized silica gel; sodium hydrogencarbonate; sodium bromide in water; acetone

Electrolysissolid phase reaction;

Kuroboshi, Manabu; Goto, Kentaro; Tanaka, Hideo

Synthesis, 2009 , # 6 art. no. F20808SS, p. 903 - 908 Title/Abstract

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59%

Stage #1: With pyridine; ruthenium trichloride; sodium hydride; 1,3-di(propan-2-yl)-1H-imidazol-3-ium bromide in toluene

24 h; Inert atmosphereReflux; Stage #2: in toluene

Ghosh, Subhash Chandra; Hong, Soon Hyeok

European Journal of Organic Chemistry, 2010 , # 22 p. 4266 - 4270 Title/Abstract

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58%

50%

Jefford, Charles W.; Wang, Ying

Journal of the Chemical Society, Chemical Communications, 1988 , # 10 p. 634 - 635 Title/Abstract

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With tert.-butylhydroperoxide; 3 A molecular sieve; zircornium(IV)

Krohn, Karsten; Vinke, Ingeborg; Adam, Horst

With potassium permanganate; copper(II) sulfate in dichloromethane

n-propoxide in dichloromethane

T=60°C; 48 h;

Journal of Organic Chemistry, 1996 , vol. 61, # 4 p. 1467 - 1472 Title/Abstract

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44%

With lt;(2,2'-bipyridine)(2,2':6',2''-terpyridine)RuOgt;2+

20 h; Ambient temperaturebuffer; electrooxidation: 56 mA current;

Navarro, Marcelo; De Giovani, Wagner F.; Romero, Jose R.

Tetrahedron, 1991 , vol. 47, # 4-5 p. 851 - 857 Title/Abstract

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T=200°C; Erhitzen mit einem Chrom(III)-oxid enth. KupferKatalysator;

Reppe et al.

Justus Liebigs Annalen der Chemie, 1955 , vol. 596, p. 1,158, 178 Full Text View citing articles Show Details

mit Hilfe von Acetobacter-Kulturen;

Weinessigfabr. A. Enenkel

Patent: DE929543 , 1949 ; Full Text Show Details

80 % Chromat.

With copper(II) oxide

T=200°C; 15 h; Further byproducts given;

Berthon, Bruno; Forestiere, Alain; Leleu, Gerard; Sillion, Bernard

Tetrahedron Letters, 1981 , vol. 22, # 41 p. 4073 - 4076 Title/Abstract

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100 % Chromat.

With acetone; dihydridotetrakis(triphenylphosphine)ruthenium(II) in toluene

T=180°C; 3 h;

Murahashi, Shun-Ichi; Ito, Kei-ichiro; Naota, Takeshi; Maeda, Yoshihiro

Tetrahedron Letters, 1981 , vol. 22, # 52 p. 5327 - 5330 Title/Abstract

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74 % Turnov.

With bromobenzene; potassium carbonate; palladium diacetate; triphenylphosphine in DME

T=85°C; 12 h;

Tamaru, Yoshinao; Yamada, Yoshimi; Inoue, Kenji; Yamamoto, Youichi; Yoshida, Zen-ichi

Journal of Organic Chemistry, 1983 , vol. 48, # 8 p. 1286 - 1292 Title/Abstract

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With dihydrogen peroxide; tricetylpyridinium-12tungstophosphate in tert-butyl alcohol

T=82°C; 24 h; Heating; Yield given;

Yamawaki, K.; Nishihara, H.; Yoshida, T.; Ura, T.; Yamada, H.; et al.

Synthetic Communications, 1988 , vol. 18, # 8 p. 869 - 876 Title/Abstract

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66 % Chromat.

With [.pi.-C5H5N(+)(CH2)15CH3]3(PMo12O40)(3-) in benzene

2 h; Heating;

Ishii, Yasutaka; Yamawaki, Kazumasa; Yoshida, Tsutomu; Ura, Toshikazu; Ogawa, Masaya

Journal of Organic Chemistry, 1987 , vol. 52, # 9 p. 1868 - 1870 Title/Abstract

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With tris(cetyl)pyridinium 12-tungstophosphate; dihydrogen peroxide in tert-butyl alcohol

24 h; Heatingother α,ω-diols; var. solvents and reagents; Product distribution;

Ishii, Yasutaka; Yoshida, Tsutomu; Yamawaki, Kazumasa; Ogawa, Masaya

Journal of Organic Chemistry, 1988 , vol. 53, # 23 p. 5549 - 5552 Title/Abstract

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With cyclohexanone; [(C6H5)3P]3Ru(CO)(Cl)H

T=140°C; 20 h; hydrogen transfer; further carbonyl compounds, further ruthenium(II) catalysts;

Marcec, Radovan

Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984 , vol. 39, # 12 p. 1823 - 1824 Title/Abstract

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65 % Chromat.

With oxoammonium resin in dichloromethane

T=20°C; 1 h;

Weik, Steffen; Nicholson, Graeme; Jung, Gnther; Rademann, Jrg

Angewandte Chemie - International Edition, 2001 , vol. 40, # 8 p. 1436 - 1439 Title/Abstract

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With Zn-Cu catalyst

T=210°C;

Zhu, Yu-Lei; Xiang, Hong-Wei; Wu, Gui-Sheng; Bai, Liang; Li, Yong-Wang

Chemical Communications, 2002 , # 3 p. 254 - 255 Title/Abstract

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83 % Chromat.

With α,α,α-trifluorotoluene; oxygen; Ru*Co(2+)*2OH(1-)*CeO2

T=80°C; 6 h; atmospheric pressure;

Ji, Hongbing; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi

Tetrahedron Letters, 2002 , vol. 43, # 40 p. 7179 - 7183 Title/Abstract

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Stage #1: With sodium hypochlorite; acetic acid in water; benzene

Seleznev; Zorina; Trifonova; Zorin; Rakhmankulov

Russian Journal of Organic Chemistry, 2002 , vol. 38, # 7 p. 1064 - 1065 Title/Abstract

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T=0°C;

Stage #2: in benzene

T=20°C;

99 % Spectr.

With air; aluminum hydroxide-supported palladium nanoparticles in toluene

T=110°C; 16 h;

Min, Serk Kwon; Kim, Namdu; Cheon, Min Park; Jae, Sung Lee; Kyung, Yeon Kang; Park, Jaiwook

Organic Letters, 2005 , vol. 7, # 6 p. 1077 - 1079 Title/Abstract

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97 % Chromat.

With 2,6-dimethylpyridine; potassium hydroxide; potassium hexacyanoferrate(III); TEMPO polystyrene resin in toluene

T=20°C; 3.5 h;

Kashiwagi, Yoshitomo; Ikezoe, Hiroshi; Ono, Tetsuya

Synlett, 2006 , # 1 art. no. U28805ST, p. 69 - 72 Title/Abstract

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100 % Chromat.

With iodosylbenzene; potassium bromide in water

3 h; sonication; Product distribution; Further Variations:Reagents;

Tohma, Hirofumi; Maegawa, Tomohiro; Takizawa, Shinobu; Kita, Yasuyuki

Advanced Synthesis and Catalysis, 2002 , vol. 344, # 3-4 p. 328 - 337 Title/Abstract

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99 % Spectr.

With Ph2P(CH2)2NH2; potassium tert-butylate in acetone

T=30°C; 1 h;

Ito, Masato; Osaku, Akihide; Shiibashi, Akira; Ikariya, Takao

Organic Letters, 2007 , vol. 9, # 9 p. 1821 - 1824 Title/Abstract

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With air; gold; titanium(IV) oxide in various solvent(s) P=9375.94 Torr; Product distribution; Further Variations:TemperaturesCatalysts;

Huang, Jie; Dai, Wei-Lin; Li, Hexing; Fan, Kangnian

Journal of Catalysis, 2007 , vol. 252, # 1 p. 69 - 76 Title/Abstract

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With oxygen; potassium carbonate; PVP-stabilized 1:3 Au:Pd nanoparticles in water

T=61.84°C; P=760.051 Torr; Product distributionKinetics;

Hou, Wenbo; Dehm, Nicole A.; Scott, Robert W.J.

Journal of Catalysis, 2008 , vol. 253, # 1 p. 22 - 27 Title/Abstract

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With hydrogen

T=220°C; Atmospheric pressure; Product distribution / selectivity; Hide Experimental Procedure

ISU CHEMICAL CO., LTD.

Patent: WO2009/82086 A1, 2009 ; Location in patent: Page/Page column 13-15 ; Title/Abstract

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6:

A tubular reactor with a diameter of 2.54 cm and length of 15.24 cm was filled with 9Og of catalyst B, and an electrical heating tape was adhered to the outside of the reactor to maintain reaction temperature at 220 °C .Reactant 1,4-butandiol was introduced into the bottom of the reactor (bottom-up) through a delivery pump at WHSV of 1.0 hr"1. The mole ratio of 1,4-butandiol and hydrogen was maintained at 1 :2, and reaction pressure was maintained at atmosphere. After the reaction was completed, selectivity for γ-butyrolactone and the conversion rate of 1,4-butandiol were analyzed by gas chromatography. As results, γ-butyrolactone selectivity of 99.32percent was obtained, and the conversion rate of1,4-butandiol was 99.21percent. <n="15"/>Examples 7 to 13: The first step reaction γ-Butyrolactone was prepared by the same procedure as Example 6, except that reaction pressure, reaction temperature, WHSV, and mole ratio were changed as described in the following Table 3. [Table 3]

With Cu1.5Mn1.5O4 T=200°C; P=1690.94 Torr; 24 h; Product distribution / selectivity; Hide Experimental Procedure

BASF CATALYSTS LLC

Patent: US2010/121080 A1, 2010 ; Location in patent: Page/Page column 5-7 ; Title/Abstract

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3:

Conversion of BDO to GLB is done in the gas phase at elevated temperature and pressure. BDO is supplied as a liquid and is vaporized prior to coming into contact with the catalyst. In one embodiment, the temperature is from about 150 to about 300° C. In another embodiment, the temperature is from about 175 to about 275° C. In yet another embodiment, the temperature is from about 185 to about 250° C. In one embodiment, the conversion of BDO to GLB is performed by contacting the inventive catalyst with either neat BDO or a mixture containing BDO in the gas or liquid phase. In another embodiment, the conversion of BDO to GLB is performed by passing neat BDO or a mixture of BDO in the gas or liquid phase at a constant or variable rate.Similarly, the inventive catalyst can perform over a range of pressure. In one embodiment, the pressure is from about 10 to about 150 psig. In one embodiment, the pressure is from about 20 to about 200 psig. In yet another embodiment, the pressure is from about 30 to about 90 psig. The rate of BDO supplied to the catalyst can be described in terms of liquid hourly space velocity, which is defined as the mass of BDO supplied per unit mass of catalyst per hour. In one embodiment, LHSV is from about 0.1 to about 3 hr-1. In another embodiment, LHSV is from about 0.2 to about 2 hr-1. In yet another embodiment, LHSV is from about 0.4 to about 1.5 hr-1.The conversion of BDO to GLB is a dehydrogenation reaction that produces one mole of GLB and two moles of hydrogen gas per mole of BDO. However, competing side reactions are also catalyzed at low rates. The product stream may contain in addition to GLB, tetrahydrofuran (THF), water, acetal, butanol, and butyric acid among other components. In one embodiment, the conversion of BDO to GLB is over about 90percent. In another embodiment, the conversion of BDO to GLB is over about 95percent. In yet another embodiment, the conversion of BDO to GLB is over 99percent.The dehydrogenation reaction of BDO to GLB does not require hydrogen to proceed. Nevertheless, hydrogen is typically included in the gas phase passed over the catalyst in order to keep metal sites in the catalyst reduced. The rate of hydrogen supplied can be described in terms of gas hourly space velocity (GHSV), which is mass of hydrogen per unit mass of catalyst per hour. In one embodiment, GHSV for hydrogen gas is from about 500 to about 2500 hr-1. In another embodiment, GHSV for hydrogen gas is from about 750 to about 2000 hr-1. In yet another embodiment, GHSV for hydrogen gas is from about 1000 to 1500 hr-1.

With oxygen; sodium acetate in water

T=130°C; 20 h; Autoclave;

Wang, Liang; Meng, Xiangju; Wang, Bin; Chi, Wenyang; Xiao, Feng-Shou

Chemical Communications, 2010 , vol. 46, # 27 p. 5003 - 5005 Title/Abstract

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T=250°C; P=760.051 Torr; 400 h; Inert atmosphere;

Hwang, Dong Won; Kashinathan, Palraj; Lee, Jong Min; Lee, Jeong Ho; Lee, U-Hwang; Hwang, Jin-Soo; Hwang, Young Kyu; Chang, Jong-San

Green Chemistry, 2011 , vol. 13, # 7 p. 1672 - 1675 Title/Abstract

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With RuCl2(2-aminomethylpyridine)(dppf); potassium hydoxide in toluene

T=125°C; 4 h; Inert atmosphere;

Schley, Nathan D.; Dobereiner, Graham E.; Crabtree, Robert H.

Organometallics, 2011 , vol. 30, # 15 p. 4174 - 4179 Title/Abstract

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148 mg

With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4cyclopentadien-1-one)-μhydrotetracarbonyldiruthenium(II); Co(NMe-salpr); 2,6-dimethoxy-pquinone in chlorobenzene

T=80°C; 24 h;

Endo, Yoshinori; Baeckvall, Jan-E.

Chemistry - A European Journal, 2011 , vol. 17, # 45 p. 12596 - 12601 Title/Abstract

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86 %Spectr.

With [RuH(.eta.2-BH4)(2-di-tert-butylphosphinomethyl-6diethylaminomethylpyridine)] in toluene

T=115°C; 48 h; Inert atmosphere;

Zhang, Jing; Balaraman, Ekambaram; Leitus, Gregory; Milstein, David

Organometallics, 2011 , vol. 30, # 21 p. 5716 - 5724 Title/Abstract

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With oxygen in toluene

T=80°C; P=760.051 Torr; 4 h;

Chen, Gongzhou; Wu, Shijian; Liu, Hongli; Jiang, Huanfeng; Li, Yingwei

Green Chemistry, 2013 , vol. 15, # 1 p. 230 - 235 Title/Abstract

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100 %Chromat.

With potassium tert-butylate; C29H30ClNOP2Ru(1+) in toluene

3 h; RefluxInert atmosphere; Product distribution / selectivity; Hide Experimental Procedure

TAKASAGO INTERNATIONAL CORPORATION; TOUGE, Taichiro; AOKI, Kunie; NARA, Hideki; KURIYAMA, Wataru

Patent: WO2012/144650 A1, 2012 ; Location in patent: Page/Page column 52-53 ; Title/Abstract

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34:

The ruthenium complex 2 which has been produced in the Example 1 and KO'Bu were added to a Schlenk flask in which boiling chips are added. Subsequently, the substratedescribed the Table 6 below and solvent were added thereto. The mixture was then stirred under nitrogen stream. The results are given in the following Table 6.

88 %Chromat.

With HRu(1,3-bis(6'-methyl-2'-pyridylimino)isoindolate)(PPh3)2 in toluene

24 h; Inert atmosphereSchlenk techniqueReflux; chemoselective reaction;

Tseng, Kuei-Nin T.; Kampf, Jeff W.; Szymczak, Nathaniel K.

Organometallics, 2013 , vol. 32, # 7 p. 2046 - 2049 Title/Abstract

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With gold supported on titanium dioxide; oxygen; sodium methylate in methanol

T=40°C; P=2250.23 Torr; 24 h; TemperatureTimeReagent/catalyst;

Brett, Gemma L.; Miedziak, Peter J.; He, Qian; Knight, David W.; Edwards, Jennifer K.; Taylor, Stuart H.; Kiely, Christopher J.; Hutchings, Graham J.

ChemSusChem, 2013 , vol. 6, # 10 p. 1952 - 1958 Title/Abstract

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With horse-liver alcohol dehydrogenase; 1-(4-hydroxy-3,5dimethoxy-phenyl)-ethanone; laccase from Myceliopthora thermophila in aq. buffer T=30°C; pH=8; 24 h; Enzymatic reaction;

Kara, Selin; Spickermann, Dominik; Schrittwieser, Joerg H.; Weckbecker, Andrea; Leggewie, Christian; Arends, Isabel W. C. E.; Hollmann, Frank

ACS Catalysis, 2013 , vol. 3, # 11 p. 2436 - 2439 Title/Abstract

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67 %Spectr.

With [Cp*Ir(6,6’-dihydroxy-2,2’-bipyridine)(H2O)] (SO3CF3)2; sodium hydrogencarbonate in water

20 h; Inert atmosphereRefluxGreen chemistry;

Fujita, Ken-Ichi; Ito, Wataru; Yamaguchi, Ryohei

ChemCatChem, 2014 , vol. 6, # 1 p. 109 - 112 Title/Abstract

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94 %Chromat.

With Oxonereg;; 2-iodo-3,4,5,6-tetramethylbenzoic acid in water; acetonitrile

T=45 - 60°C; 17 h; Green chemistry; Hide Experimental Procedure

Jhulki, Samik; Seth, Saona; Mondal, Manas; Moorthy, Jarugu Narasimha

Tetrahedron, 2014 , vol. 70, # 13 p. 2286 - 2293 Title/Abstract

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5.2 General procedure for catalytic oxidation of diols to lactones using TetMe-IA via in situ-generated TetMe-IBX

General procedure: In a typical experiment, a round bottom flask containing 4–6mL of acetonitrile/water mixture (1:1) was charged with 0.5–1.0mmol of the diol, 5molpercent of TetMe-IA, and oxone (2equiv). The resulting mixture was stirred at rt for benzylic diols and at 45°C for aliphatic diols. At the end of the reaction, as judged from TLC analysis, little water was added to dissolve the inorganic salts, and the organic matter was extracted with EtOAc at least two times. The combined extract was dried over anhydrous Na2SO4, concentrated in vacuo to obtain the crude product, which was subjected to silica-gel column chromatography using ethyl acetate/pet ether to isolate the pure product.

96 %Chromat.

With carbon-nitrogen embedded cobalt nanoparticles (800); air in hexane

T=25°C; P=760.051 Torr; 96 h;

Zhong, Wei; Liu, Hongli; Bai, Cuihua; Liao, Shijun; Li, Yingwei

ACS Catalysis, 2015 , vol. 5, # 3 p. 1850 - 1856 Title/Abstract

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80 %Spectr.

With (PNPiPr)Fe(H)(CO)BH4; potassium carbonate in tert-Amyl alcohol

T=150°C; 5 h; Inert atmosphereGreen chemistry;

Pea-Lpez, Miguel; Neumann, Helfried; Beller, Matthias

ChemCatChem, 2015 , vol. 7, # 5 p. 865 - 871 Title/Abstract

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8

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90%

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With sulfuric acid in chloroform

T=60°C; pH=0.5; 1 h; pH-valueSolventTemperature; Hide Experimental Procedure

Rx-ID: 198645 Find similar reactions

Samsung Electronics Co., Ltd.; Lee, Kyunghae; Lee, Mooho; Chwae, Jun; Park, Jinhwan; Lee, Jongmin; Cho, Kwangmyung; Park, Jaechan

Patent: US2015/259311 A1, 2015 ; Location in patent: Paragraph 0046 ; Title/Abstract

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1:Example 1Conversion of 4-RB to GBL Under Acid Condition in the Presence of Solvent

10031] E. Coli producing 4-RB was cultured in a medium (13.5 g KR2PO4, 4 g (NR4)2RP04, 1.7 g citric acid, 1.4 g MgSO4.7R20, Yeast extract 2 g, MOPS 21 g, 10 mE trace metal solution (10 g Fe504.7R20, 1.35 g CaC12, 2.25 g Zn504.7R20, 0.5 g Mn504.4R20, 1 g Cu504.5R20, 0.106 g (NR4)5Mo7O24.4R20, 0.23 gNa2B4O7.10R20, 35percent RC1 10 mE per 1 L distilled water) per 1 L distilled water) for 200 hours to obtain 9-12 (w/v) percent 4-RB containing culture solution (pR about 6.-7.0). 95 (w/v) percent sulthric acid was added to 100 ml of the culture solution so that pR of the culture solutionwas 0.5, 1.0,2.0, or 4.0 in each ofthe 100 ml ofthe culture solution as a sample. The culture solution was maintained at room temperature for 1 hour to allow 4-RB to convert to GBL. After 1 hour, each of the samples was placed in RPLC (Waters, Colunm: C18, Room Temperature (25°C.), UV: 195 nm, Flow: 1.0 ml/min, Injection volume: 2 tL, Buffer: 25 mM KR2PO4) and GC (Younglin G C, Detector: FID) to measure 4-RB and GBL. Table 1 shows the effect of pR on conversion of 4-RB to GBL.

bei der Destillation;

Fittig; Chanlarow

Justus Liebigs Annalen der Chemie, 1884 , vol. 226, p. 331,332 Full Text View citing articles Show Details

With hydrochlorid acid in ethanol

T=25°C; Rate constant;

Storm,D.R.; Koshland,D.E.

Journal of the American Chemical Society, 1972 , vol. 94, p. 5805 - 5814 Full Text View citing articles Show Details

Hide Details

9

With cis-nitrous acid

T=25°C; Rate constant;

Austin,A.T.; Howard,J.

Journal of the Chemical Society, 1961 , p. 3284 - 3289 Full Text View citing articles Show Details

With hydrochlorid acid

T=35°C; Equilibrium constant; Further Variations:Temperatures;

Perez-Prior, M. Teresa; Manso, Jose A.; Del Pilar Garcia-Santos; Calle, Emilio; Casado, Julio

Journal of Organic Chemistry, 2005 , vol. 70, # 2 p. 420 - 426 Title/Abstract

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Rx-ID: 227291 Find similar reactions

Gryszkiewicz-Trochimowski

Recueil des Travaux Chimiques des Pays-Bas, 1947 , vol. 66, p. 428 Full Text Show Details

10

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With sodium ethanolate

Rx-ID: 227293 Find similar reactions

Marvel; Birkhimer

Journal of the American Chemical Society, 1929 , vol. 51, p. 261 Full Text View citing articles Show Details

A

B

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11

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T=205°C;

Willstaetter

Chemische Berichte, 1902 , vol. 35, p. 602 Full Text Show Details

12

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With 1,4-dioxane; anhydrous sodium borate

With diethyl ether; boric acid trimethyl ester; sodium

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Rx-ID: 242643 Find similar reactions

Chaikin; Brown

Journal of the American Chemical Society, 1949 , vol. 71, p. 122,124 Full Text View citing articles Show Details

Schlesinger; Brown

Patent: US2683721 , 1952 ; Full Text Show Details

A

B

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13

Synthesize Find similar Rx-ID: 269738 Find similar reactions

Fittig; Roeder

Justus Liebigs Annalen der Chemie, 1885 , vol. 227, p. 19 Full Text Show Details

A

B

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14

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Willstaetter

Chemische Berichte, 1902 , vol. 35, p. 602 Full Text Show Details

15

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Rx-ID: 659456 Find similar reactions

T=170°C; Hydrogenation.an Palladium-Katalysatoren;

Froeschl; Maier

Monatshefte fuer Chemie, 1932 , vol. 59, p. 256,271, 272 Full Text View citing articles Show Details

T=220°C; Hydrogenation.an Palladium-Katalysatoren;

Froeschl; Danoff

Journal fuer Praktische Chemie (Leipzig), 1936 , vol. <2>144, p. 221 Full Text Show Details

16

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With potassium cyanide; ethanol

anschl. mit wss. KOH;

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Rx-ID: 791713 Find similar reactions

Boorman; Linstead

Journal of the Chemical Society, 1933 , p. 577,580 Full Text View citing articles Show Details

17

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With cyclohexane; Nitrous oxide

T=300°C; P=220652 Torr;

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Rx-ID: 792398 Find similar reactions

Buckley; Levy

Journal of the Chemical Society, 1951 , p. 3016 Full Text View citing articles Show Details

18

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With aluminium trichloride; chloroform; 2-chloro-ethanol

anschl. Erwaermen mit wss. HCl;

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Rx-ID: 797598 Find similar reactions

Michael; Weiner

Journal of the American Chemical Society, 1936 , vol. 58, p. 999,1002 Full Text View citing articles Show Details

Raha

Journal of the American Chemical Society, 1954 , vol. 76, p. 622 Full Text View citing articles Show Details

19

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With tetreamethyl ammonium hydroxide in dimethyl sulfoxide

T=18 - 50°C; Kinetics;

Rx-ID: 1186533 Find similar reactions

Mandolini,L.

Journal of the American Chemical Society, 1978 , vol. 100, p. 550 - 554 Full Text View citing articles Show Details

20

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Rx-ID: 1455889 Find similar reactions

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With hydrogenchloride; potassium-sodium; 18-crown-6 ether

Yield given. Multistep reaction;

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Jedlinski, Zbigniew; Misiolek, Andrzej; Jankowski, Andrzej; Janeczek, Henryk

Journal of Organometallic Chemistry, 1992 , vol. 433, # 3 p. 231 - 239 Title/Abstract

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21

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Rx-ID: 1455891 Find similar reactions

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70%

With dicobalt octacarbonyl; triruthenium dodecacarbonyl in ethylene glycol dimethyl ether

T=190°C; P=45600 Torr; 48 h;

Wang, Ming-De; Calet, Serge; Alper, Howard

Journal of Organic Chemistry, 1989 , vol. 54, # 1 p. 20 - 21 Title/Abstract

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With ({1,2-di[(2-OH-3,5-ditBu)PhCH=N]Ph}Al[THF]2)+[Co(CO)4]- in toluene

T=80°C; P=10343 Torr; 24 h;

Getzler, Yutan D. Y. L.; Kundnani, Vinod; Lobkovsky, Emil B.; Coates, Geoffrey W.

Journal of the American Chemical Society, 2004 , vol. 126, # 22 p. 6842 - 6843 Title/Abstract

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22

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Rx-ID: 1496869 Find similar reactions

52%

With 3 A molecular sieve; pyridinium chlorochromate in dichloromethane

8 h; Heatingother substrates; reactivity;

Baskaran, S.; Chandrasekaran, S.

Tetrahedron Letters, 1990 , vol. 31, # 19 p. 2775 - 2778 Title/Abstract

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52%

With 3 A molecular sieve; pyridinium chlorochromate in dichloromethane

8 h; Heating;

Baskaran, S.; Chandrasekaran, S.

Tetrahedron Letters, 1990 , vol. 31, # 19 p. 2775 - 2778 Title/Abstract

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23

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57%

With dipyridinium dichromate in benzene

T=80°C; 4 h;

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Rx-ID: 1514377 Find similar reactions

Baskaran, S.; Islam, I.; Raghavan, Malini; Chandrasekaran, S.

Chemistry Letters, 1987 , p. 1175 - 1178 Title/Abstract

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24

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Rx-ID: 1537302 Find similar reactions

55%

With pyridinium chlorochromate in dichloromethane

T=40°C; 6 h;

Baskaran, S.; Chandrasekaran, S.

Tetrahedron Letters, 1990 , vol. 31, # 19 p. 2775 - 2778 Title/Abstract

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47%

With Celite; pyridinium chlorochromate in dichloromethane

Baskaran, Sundarababu; Islam, Imadul; Chandrasekaran, Srinivasan

3 h; Heating;

Journal of Chemical Research, Miniprint, 1992 , p. 2213 - 2246 Title/Abstract

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25

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Rx-ID: 1546701 Find similar reactions

21 % Chromat.

With dihydridotetrakis(triphenylphosphine)ruthenium(II) in diethylene glycol dimethyl ether

T=145°C; 3 h; other catalysts, var. temp. and times; Product distribution;

Shvo, Youval; Blum, Yigal; Reshep, Deborah

Journal of Organometallic Chemistry, 1982 , vol. 238, # 4 p. C79 - C81 Title/Abstract

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With hydrogen; copper oxides/alumina in water

T=220°C; P=760.051 Torr; Product distribution / selectivity; Hide Experimental Procedure

BASF SE; PINKOS, Rolf; OSETSKA, Olga; KOeNIGSMANN, Lucia; BASF JAPAN LTD.

Patent: WO2012/95777 A1, 2012 ; Location in patent: Page/Page column 10-11 ; Title/Abstract

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5:

Examples 1 -6 below were carried out using pure 1 ,4-butynediol as 40percent strength by weight aqueous solution at atmospheric pressure. The butynediol solution was pumped continuously into an externally heated tube (diameter 2.7 cm). The tube was charged with glass rings (30 ml) in the upper region. This zone served as vaporization section in which 1 ,4-butynediol/water and hydrogen (300 liter/h) were heated and passed in gaseous form into a second zone in the reactor tube in which the catalyst was located (20 ml). After the reactor tube, the gaseous reactor output was cooled to about 20°C and product which condensed out was collected. The offgas was passed through a cold trap at -78°C and further product was condensed out in this way. The two condensates were combined for the purposes of analysis. The catalysts were activated in a stream of hydrogen before the reaction. The results are shown in table 1

26

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Rx-ID: 1562511 Find similar reactions

95%

With DMBI in tetrahydrofuran

4 h; Heating;

Chikashita, Hidenori; Ide, Hisao; Itoh, Kazuyoshi

Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5400 - 5405 Title/Abstract

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95%

With nickel in tetrahydrofuran

T=20°C; 0.75 h;

Barrero; Alvarez-Manzaneda; Chahboun; Meneses; Romera

Synlett, 2001 , # 4 p. 485 - 488 Title/Abstract

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90%

With triethyl borane; tri-n-butyl-tin hydride in hexane; toluene

T=-78°C; 0.5 h;

Miura, Katsukiyo; Ichinose, Yoshifumi; Nozaki, Kyoko; Fugami, Keigo; Oshima, Koichiro; Utimoto, Kiitiro

Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 1 p. 143 - 147 Title/Abstract

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82%

With triphenylphosphine hydroiodide in acetonitrile

6 h; Ambient temperature;

Kamiya, Naoshi; Tanmatu, Hiroshi; Ishii, Yasutaka

Chemistry Letters, 1992 , p. 293 - 296 Title/Abstract

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A

B

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27

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A: 62 % Chromat.

B: 20 % Chromat.

With zirconium oxide in isopropyl alcohol

T=280°C; also other anhydrides, var. alcohols; Product distribution;

Takahashi, Kyoko; Shibagaki, Makoto; Matsushita, Hajime

Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 1 p. 262 - 266 Title/Abstract

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28

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90.1%

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With hydrogen in 1,4-dioxane

T=199.84°C; P=37503.8 Torr; 5 h; Catalytic behaviorActivation energy; Temperature; Hide Experimental Procedure

Rx-ID: 1567495 Find similar reactions

Chung, Sang-Ho; Eom, Hee-Jun; Kim, Min-Sung; Lee, Myung Suk; Lee, Kwan-Young

Journal of Nanoscience and Nanotechnology, 2013 , vol. 13, # 11 p. 7701 - 7706 Title/Abstract

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Hydrogenation of succinic anhydride was conducted ina 150 mL high-pressure batch reactor with a magnetic stirrer.The detailed reaction procedure has been previouslydescribed.28 Before the reaction, 0.3 g of the prepared catalystwas reduced under hydrogen gas (ultra high purity,>99.999percent) at 20 bar and 573 K for 2 h (RuNPs/SiO2-300R). After the catalyst reduction, the reaction vesselwas charged with 0.5 g of succinic anhydride and 50 mLof 1,4-dioxane. The remaining air was removed by purging the reactor with hydrogen gas, and the pressure was increased to 10 bar with H2. Once the reactor was heated to and maintained the reaction temperature, the pressure was raised to 50 bar with gaseous H2, and the reactionmixture was stirred at 750 rpm for 6 h. To follow theprogress of the reaction, approximately 0.3 mL of liquid samples were collected through the sampling line, which was connected to the bottom of reaction vessel. During the sampling procedure, the reaction pressure was maintained by continuously introducing hydrogen gas from the high-pressure gas reservoir.

68%

With lithium borohydride in tetrahydrofuran

0.25 h;

Narasimhan, Srinivasan

Heterocycles, 1982 , vol. 18, p. 131 - 135 Title/Abstract

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68%

With lithium borohydride in tetrahydrofuran

T=25°C; 0.25 h; other cyclic anhydrides; Mechanism;

Narasimhan, Srinivasan

Heterocycles, 1982 , vol. 18, p. 131 - 135 Title/Abstract

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100 % Turnov.

With Li (cyanomethyl)trihydroborate-dioxane in tetrahydrofuran

1.) 30 min room temperature 2.) 1 h reflux; reduction by other Li (α-cyanoalkyl)trihydroborates;

Mittakanti, Mallaiah; Peters, John L.; Morse, Karen W.

Journal of Organic Chemistry, 1990 , vol. 55, # 14 p. 4464 - 4466 Title/Abstract

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With hydrogen; Ru(acac)3; tri-n-octyl phosphine; toluene-4-sulfonic acid in various solvent(s) T=200°C; P=22501.8 Torr; 2 h;

Hara, Yoshinori; Wada, Keisuke

Chemistry Letters, 1991 , # 4 p. 553 - 554 Title/Abstract

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With hydrogen; Ru(acac)3; tri-n-octyl phosphine; toluene-4-sulfonic acid in various solvent(s) T=200°C; P=22501.8 Torr; 2 h; activity and selectivity of (other) catalysts, other strong acids; other anhydrides;

Hara, Yoshinori; Wada, Keisuke

Chemistry Letters, 1991 , # 4 p. 553 - 554 Title/Abstract

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With hydrogen; tris(triphenylphosphine)ruthenium(II) chloride in various solvent(s) T=170°C; Hydrogenation; P=750.06 Torr; Product distribution; Further Variations:CatalystsSolvents;

Hara, Yoshinori; Kusaka, Haruhiko; Inagaki, Hiroko; Takahashi, Kazunari; Wada, Keisuke

Journal of Catalysis, 2000 , vol. 194, # 2 p. 188 - 197 Title/Abstract

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With hydrogen; di-μ-chloro-bis(η4-1,5cyclooctadiene)diiridium; (R)-Ph-MeOBIPHEP in tetrahydrofuran

T=20 - 100°C; P=60006 Torr; 15.3333 h; Product distribution / selectivity; Hide Experimental Procedure

SOLVIAS AG

Patent: WO2006/108802 A1, 2006 ; Location in patent: Page/Page column 26-29 ; Title/Abstract

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8:

Example 8: Preparation of γ-butyrolactone of the formula; ^ - 'Under an argon atmosphere, 6.74 mg (0.01 mmol) [lr(1,5-cyclooctadiene)CI]2 and 13.41 mg (0.021 mmol) of (R)-2,2'-diphenylphosphino-6,6'-dimethoxy-1 ,1'-biphenyl and 5 ml of tetrahydrofuran are introduced in succession into a 10 ml Schlenk vessel. This solution is stirred at room temperature for 15 minutes. 200.3 mg (2 mmol) of succinic anhydride and EPO <DP n="30"/>5 ml of tetrahydrofuran are introduced under an argon atmosphere into a second Schlenk vessel. The substrate solution is stirred for 5 minutes. The anhydride/lr ratio is 100. The catalyst solution and the substrate solution are subsequently transferred in succession by means of a steel capillary into a 50 ml steel autoclave filled with an argon atmosphere. The autoclave is closed and the argon atmosphere is replaced by a hydrogen atmosphere in 4 flushing cycles (20 bar/1 bar). The hydrogen pressure is set to 80 bar, the stirrer is switched on and the autoclave is heated to 1000C. After 15 hours, the autoclave is cooled and depressurized. The conversion is determined by gas chromatography. The conversion is 100percent.

With hydrogen; di-μ-chloro-bis(η4-1,5cyclooctadiene)diiridium; (R)-Ph-MeOBIPHEP in tetrahydrofuran

T=100°C; P=60006 Torr; 15 h; Inert atmosphereAutoclave; Hide Experimental Procedure

Spindler, Felix

Patent: US2009/275761 A1, 2009 ; Location in patent: Page/Page column 13-14 ; Title/Abstract

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8:

EXAMPLE 6Preparation of 3-oxabicyclo[3.4.0]nonan-2-one of the formula Under an argon atmosphere, 6.74 mg (0.01 mmol) of [Ir(1,5-cyclooctadiene)Cl]2 and 24.21 mg (0.021 mmol) of (S)-L4 and 5 ml of tetrahydrofuran are introduced in succession into a 10 ml Schlenk vessel. This solution is stirred at room temperature for 15 minutes. cis-3-Oxabicyclo[3.4.0]nonane-2,4-dione and 5 ml of tetrahydrofuran are introduced under an argon atmosphere into a second Schlenk vessel. The substrate solution is stirred for 5 minutes. The anhydride/Ir ratio is 100. The catalyst solution and the substrate solution are subsequently transferred in succession by means of a steel capillary into a 50 ml steel autoclave under an argon atmosphere. The autoclave is closed, the argon atmosphere is replaced by a hydrogen atmosphere in 4 flushing cycles (20 bar/1 bar). The hydrogen pressure is set to 80 bar and the autoclave is heated to 100° C. while stirring. After 15 hours, the autoclave is cooled and depressurized. The conversion and the enantiomeric purity are determined by gas chromatography. The conversion is 100percent and the enantiomeric purity of the 3-oxabicyclo[3.4.0]nonan-2-one formed is 87percent ee.

With hydrogen

T=220°C; P=750.075 Torr; Reagent/catalyst;

Regenhardt, Silvina A.; Meyer, Camilo I.; Garetto, Teresita F.; Marchi, Alberto J.

Applied Catalysis A: General, 2012 , vol. 449, p. 81 - 87 Title/Abstract

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29

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Rx-ID: 1813439 Find similar reactions

65%

With (cetyl)Me3N(1+)MnO4(1-) in chloroform

T=25°C; 4.5 h;

Rathore, Rajendra; Vankar, Padma S.; Chandrasekaran, S.

Tetrahedron Letters, 1986 , vol. 27, # 34 p. 4079 - 4082 Title/Abstract

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52%

With potassium permanganate; water; copper(II) sulfate in dichloromethane

1.) reflux, 5 min, 2.) RT, 6 h;

Baskaran, Sundarababu; Islam, Imadul; Vankar, Padma S.; Chandrasekaran, Srinivasan

Journal of the Chemical Society, Chemical Communications, 1990 , # 23 p. 1670 - 1671 Title/Abstract

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73 % Chromat.

With Oxonereg;; osmium(VIII) oxide in N,N-dimethyl-formamide

T=20°C;

Schomaker, Jennifer M.; Travis, Benjamin R.; Borhan, Babak

Organic Letters, 2003 , vol. 5, # 17 p. 3089 - 3092 Title/Abstract

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30

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Rx-ID: 1825170 Find similar reactions

83%

With hydrogenchloride; N-Nitrosomorpholine; potassium iodide in dichloromethane; water

T=22°C; 24 h;

Jorgensen, K. A.; El-Wassimy, M. T. M.; Lawesson, S. -O.

Tetrahedron, 1983 , vol. 39, # 3 p. 469 - 474 Title/Abstract

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100 % Chromat.

With di(n-butyl)tin oxide in 1,4-dioxane

Heating;

Tsuda; Sato; Kakimoto; Kanemitsu

Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 4 p. 1033 - 1036 Title/Abstract

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A

B

C

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31

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32

With kieselguhr catalyst; cobalt

T=210 - 320°C; reaction selectivity; efficiency; KineticsProduct distributionRate constant;

Geiman, I. I.; Bulenkova, L. F.; Lazdin'sh, A. A.; Veinberg, A. K.; Slavinskaya, V. A.; Avots, A. A.

Chemistry of Heterocyclic Compounds (New York, NY, United States), 1981 , p. 314 - 316 Khimiya Geterotsiklicheskikh Soedinenii, 1981 , vol. 17, # 4 p. 448 - 450 Title/Abstract

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Rx-ID: 1839830 Find similar reactions

100%

With 5 wtpercent Pd nanoparticles loaded on phosphate anion exchanged [Mg6Al2(OH)16]CO3*xH2O; air T=50°C; P=760.051 Torr; 6 h; Irradiation; Reagent/catalyst;

Tana, Tana; Guo, Xiao-Wei; Xiao, Qi; Huang, Yiming; Sarina, Sarina; Christopher, Phillip; Jia, Jianfeng; Wu, Haishun; Zhu, Huaiyong

Chemical Communications, 2016 , vol. 52, # 77 p. 11567 - 11570 Title/Abstract

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88 % Chromat.

With acetone; dihydridotetrakis(triphenylphosphine)ruthenium(II) in toluene

T=180°C; 3 h;

Murahashi, Shun-Ichi; Ito, Kei-ichiro; Naota, Takeshi; Maeda, Yoshihiro

Tetrahedron Letters, 1981 , vol. 22, # 52 p. 5327 - 5330 Title/Abstract

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33

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89%

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With lt;RuH2(PPh3)4gt;; water in ethylene glycol dimethyl ether

T=140°C; 24 h;

Rx-ID: 1929551 Find similar reactions

Naota, Takeshi; Shichijo, Yasuji; Murahashi, Shun-Ichi

Journal of the Chemical Society, Chemical Communications, 1994 , # 11 p. 1359 - 1360 Title/Abstract

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34

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Rx-ID: 1936488 Find similar reactions

72%

35

With potassium carbonate; silver nitrate

120 h; Heating;

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Brown, Stephen P.; Bal, Balkrishna S.; Pinnick, Harold W.

Tetrahedron Letters, 1981 , vol. 22, # 49 p. 4891 - 4894 Title/Abstract

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85%

With potassium carbonate in tetrahydrofuran

Heating;

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Rx-ID: 1936490 Find similar reactions

Brown, Stephen P.; Bal, Balkrishna S.; Pinnick, Harold W.

Tetrahedron Letters, 1981 , vol. 22, # 49 p. 4891 - 4894 Title/Abstract

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36

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91%

With benzeneseleninic acid in dichloromethane

1.75 h;

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Rx-ID: 1943272 Find similar reactions

Back, Thomas G.; Collins, Scott; Ker, Russell G.

Journal of Organic Chemistry, 1981 , vol. 46, p. 1564 - 1570 Title/Abstract

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37

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38

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Rx-ID: 1943779 Find similar reactions

66%

With silica gel in xylene

Heating;

Tsuboi, Sadao; Muranaka, Koichi; Fujita, Hiroshi; Seko, Katsuhiko; Takeda, Akira

Heterocycles, 1984 , vol. 21, # 2 p. 602 Title/Abstract

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66 % Chromat.

With silica gel in xylene

15 h; Heating;

Tsuboi, Sadao; Fujita, Hiroshi; Muranaka, Koichi; Seko, Katsuhiko; Takeda, Akira

Chemistry Letters, 1982 , p. 1909 - 1912 Title/Abstract

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20%

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With sodium hydroxide in water

T=40 - 45°C; electrolysis, carbon electrodes;

Rx-ID: 1953383 Find similar reactions

Misra, R. A.; Sharma, B. L.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982 , vol. 21, # 4 p. 329 - 330 Title/Abstract

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39

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87%

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With hydrogenchloride

1.)r.t., 10 min 2.)reflux, 2 h;

Rx-ID: 1962265 Find similar reactions

Krasavtsev, I. I.; Basalkevich, E. D.; Matvienko, L. P.; Lozinskii, M. O.

Journal of Organic Chemistry USSR (English Translation), 1986 , p. 1046 - 1048 Zhurnal Organicheskoi Khimii, 1986 , vol. 22, # 6 p. 1163 - 1165 Title/Abstract

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40

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Rx-ID: 2007600 Find similar reactions

in hexane

T=26°C; porcine pancreatic lipase (PPL);

Gutman, Arie L.; Zuobi, Kheir; Bravdo, Tamar

Journal of Organic Chemistry, 1990 , vol. 55, # 11 p. 3546 - 3552 Title/Abstract

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With porcine pancreatic lipase (E.(1)C313) in diethyl ether

T=26°C; Yield given;

Gutman, Arie L.; Zuobi, Kheir; Boltansky, Aviv

Tetrahedron Letters, 1987 , vol. 28, # 33 p. 3861 - 3864 Title/Abstract

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A

41

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C

Find similar Rx-ID: 2147175 Find similar reactions

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A: 2% C: 38%

in benzene

T=10 - 20°C; 18 h; Irradiation;

Dupuy, Claude; Surzur, Jean-Marie

Bulletin de la Societe Chimique de France, 1980 , vol. 2, # 7-8 p. 374 - 380 Title/Abstract

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A: 2% C: 38%

in benzene

T=10 - 20°C; 18 h; Irradiationexamination of further acetylenic nitrites, reaction time; Product distribution;

Dupuy, Claude; Surzur, Jean-Marie

Bulletin de la Societe Chimique de France, 1980 , vol. 2, # 7-8 p. 374 - 380 Title/Abstract

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42

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Rx-ID: 2563952 Find similar reactions

62%

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane

T=0°C;

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract

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91 % Chromat.

With water; Ledwith–Weitz salt in acetonitrile

Ambient temperature; Product distribution;

Hoye, Thomas R.; Kurth, Mark J.; Lo, Vincent

Tetrahedron Letters, 1981 , vol. 22, p. 815 - 818 Title/Abstract

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43

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60%

With potassium carbonate in acetonitrile

12 h; Heating;

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Rx-ID: 3081540 Find similar reactions

Nakamura, Takako; Matsuyama, Haruo; Takahashi, Masaya; Kamigata, Nobumasa

Phosphorus, Sulfur and Silicon and the Related Elements, 1992 , vol. 66, # 14 p. 59 - 66 Title/Abstract

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44

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Rx-ID: 3323184 Find similar reactions

35%

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With hydrogenchloride; oxygen; copper dichloride; palladium dichloride in tetrahydrofuran

P=760 Torr; Ambient temperature;

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Alper, Howard; Leonard, Daniele

Tetrahedron Letters, 1985 , vol. 26, # 46 p. 5639 - 5642 Title/Abstract

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A

B

C

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45

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Rx-ID: 3323187 Find similar reactions

A: 36% B: 20% C: 32%

With 2-ethoxy-ethanol; 4-(N,Ndimethlyamino)pyridine; Rh6(CO)12 in water

T=80°C; P=3800 Torr; 10 h;

Kaneda, Kiyotomi; Imanaka, Toshinobu; Teranishi, Shiichiro

Chemistry Letters, 1983 , p. 1465 - 1466 Title/Abstract

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46

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Rx-ID: 3566545 Find similar reactions

With base in water; dimethyl sulfoxide

T=34°C;

Casadei, Maria Antonietta; Martino, Alessandro di; Galli, Carlo; Mandolini, Luigi

Gazzetta Chimica Italiana, 1986 , vol. 116, # 11 p. 659 - 664 Title/Abstract

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in water; dimethyl sulfoxide

T=34°C; Rate constantMechanism;

Casadei, Maria Antonietta; Martino, Alessandro di; Galli, Carlo; Mandolini, Luigi

Gazzetta Chimica Italiana, 1986 , vol. 116, # 11 p. 659 - 664 Title/Abstract

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47

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Rx-ID: 3607454 Find similar reactions

Velzen, J. C. van; Tunen, W. C. J. van; Boer, Th. J. de

Recueil des Travaux Chimiques des Pays-Bas, 1986 , vol. 105, # 7-8 p. 225 - 228 Title/Abstract

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in chloroform

8 h; Heating; Yield given;

48

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Rx-ID: 3860036 Find similar reactions

34%

With sodium peroxodisulphate in water

T=85 - 90°C; 5 h;

Nikishin, Gennady I.; Svitanko, Igor V.; Troyansky, Emmanuil I.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983 , p. 595 - 602 Title/Abstract

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With sodium peroxodisulphate in water

T=80°C; Mechanism;

Zabarev, V. E.; Toryanskii, E. I.; Nikishin, G. I.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1986 , vol. 35, # 11 p. 2413 - 2415 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986 , # 11 p. 2630 - 2633 Title/Abstract

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A

B

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49

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A: 34 %

With sodium peroxodisulphate; copper dichloride in water

Troyanskii, E. I.; Svitan'ko, I. V.; Nikishin, G. I.

Turnov.

B: 36 % Turnov.

T=85 - 90°C; 5 h;

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982 , vol. 31, # 10 p. 2041 - 2046 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982 , # 10 p. 2318 - 2325 Title/Abstract

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50

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5%

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With pyridine hydrochloride

T=150°C; 72 h;

Rx-ID: 3927286 Find similar reactions

Buttinelli, Paolo; Gargaro, Giuseppe; Loreto, M. Antonietta; Pellacani, Lucio; Tardella, Paolo A.

Gazzetta Chimica Italiana, 1985 , vol. 115, # 3 p. 155 - 158 Title/Abstract

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51

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90%

With 5 active carbon-supported ruthenium; hydrogen

T=150°C; P=26252.6 Torr;

Primo, Ana; Concepcion, Patricia; Corma, Avelino

Chemical Communications, 2011 , vol. 47, # 12 p. 3613 - 3615 Title/Abstract

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30%

With butanediamide; hydrogen in Triethylene glycol dimethyl ether

MITSUBISHI CHEMICALS CORP; TANIGUCHI, SHOHEI; IZAWA, YUSUKE; UTSUNOMIYA, MASARU

Patent: JP2015/193603 A, 2015 ; Location in patent: Paragraph 0071 - 0073 ;

T=205°C; P=6750.68 Torr; 2 h; Autoclave; Reagent/catalyst; Hide Experimental Procedure

Title/Abstract

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1:Example 1

succinic acid 5.9 g (11.8 wtpercent), 5.0 g (Ru : 400 mass ppm) ofsolution obtained by dissolving ruthenium complex having trioctyl phosphine asligand in triglyme and 39.1g triglyme as solvent were charged into an autoclave(material: SUS 316) of 100ml capacity. Nitrogen compound concentration in thereaction mixture was less than 1 mass ppm.[0072]After placing a magnetic stirrer inside the autoclave, theinside of the system was sufficiently replaced with hydrogen. The temperaturewas elevated while stirring using magnetic stirrer, when the inner temperature ofthe autoclave was reached to 205 ° C, hydrogen was inspissated to make the internalpressure to be 0.9 MPa · G (gauge pressure). Taking that time as the reaction startingtime, then hydrogenation reaction was carried out for 2 hours.After completion of the reaction, part of the resultingreaction solution was taken, and as a result of analysis by gas chromatography,the yield of gamma-butyrolactone was 29.6percent. The reaction results are shown inTable 2.

With hydrogen; Ru4(CO)8lt;OOC(CH2)2COOgt;2(PBu3)4 in 1,4dioxane

T=180°C; P=98800 Torr; 22 h; Yield given;

Matteoli, Ugo; Menchi, Gloria; Bianchi, Mario; Frediani, Piero; Piacenti, Franco

Gazzetta Chimica Italiana, 1985 , vol. 115, # 11 p. 603 - 606 Title/Abstract

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Hide Details

With hydrogen; from 4 to 104-day old non-extracted Cat-A catalyst (with nominally 1percent Ru, 6percent Re) T=250°C; P=103432 Torr; Product distribution / selectivity; Hide Experimental Procedure

Campos, Daniel; Ernst, Richard Edward

Patent: US2004/77885 A1, 2004 ; Location in patent: Page 4 ; Title/Abstract

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R; S; T; U; V; W; X; Y:Examples 19-27

[0057] Various slurry samples containing used Cat-A catalyst (with nominally 1percent Ru, 6percent Re) taken during operation and after shutdown from a continuous reactor are listed in Table 3. Prior to activity measurement, Comparative Examples R-Y were prepared by simply drying the slurry overnight in a vacuum oven with N2 purge. This treatment only removed water and volatile components, such as THF. Any foulants, such as waxes and other high boiling compounds remained on the catalyst. [0058] Examples 19-27 were prepared wherein the slurry was extracted with THF under reflux and then filtered and dried. First the slurry sample, (normally 50 g of slurry) of about 20percent solids was filtered in a Millipore funnel filter with 0.2 micrometer nylon membrane filter under vacuum (180 mm Hg) to about 50percent solids. This is a slow process (overnight) as the filter cake is very sticky. Then the filter cake was transferred to a 500 ml round bottom flask and mixed with 5 parts of THF (based on 1 part by weight of original slurry). While stirring with a magnetic stirrer, the mixture was heated under reflux for 2 hours at about 66° C. The slurry was then filtered (same type of filter as above) and the resulting cake was dried at 110° C. in a vacuum oven for at least 6 hours. [0059] All resulting samples were tested in the 300-cc batch hydrogenation reactor with pure H2 on a 7percent SAC solution at 2000 psi, 250° C. and 700 RPM. The rate of conversion of SAC to GBL and by-products was measured and reported as STY in Table 3. In the case of the Comparative Examples, the STY was corrected for the real weight of catalyst, which excluded the weight of the organics remaining in the sample after drying. Also, the STY of the Comparative Examples was corrected by subtracting the STY obtained from runs using catalyst and water.

With hydrogen; from 4 to 104-day old THF extracted Cat-A catalyst (with nominally 1percent Ru, 6percent Re) T=250°C; P=103432 Torr; Product distribution / selectivity; Hide Experimental Procedure

Campos, Daniel; Ernst, Richard Edward

Patent: US2004/77885 A1, 2004 ; Location in patent: Page 4 ; Title/Abstract

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19; 20; 21; 22; 23; 24; 25; 26; 27:Examples 19-27

[0057] Various slurry samples containing used Cat-A catalyst (with nominally 1percent Ru, 6percent Re) taken during operation and after shutdown from a continuous reactor are listed in Table 3. Prior to activity measurement, Comparative Examples R-Y were prepared by simply drying the slurry overnight in a vacuum oven with N2 purge. This treatment only removed water and volatile components, such as THF. Any foulants, such as waxes and other high boiling compounds remained on the catalyst. [0058] Examples 19-27 were prepared wherein the slurry was extracted with THF under reflux and then filtered and dried. First the slurry sample, (normally 50 g of slurry) of about 20percent solids was filtered in a Millipore funnel filter with 0.2 micrometer nylon membrane filter under vacuum (180 mm Hg) to about 50percent solids. This is a slow process (overnight) as the filter cake is very sticky. Then the filter cake was transferred to a 500 ml round bottom flask and mixed with 5 parts of THF (based on 1 part by weight of original slurry). While stirring with a magnetic stirrer, the mixture was heated under reflux for 2 hours at about 66° C. The slurry was then filtered (same type of filter as above) and the resulting cake was dried at 110° C. in a vacuum oven for at least 6 hours. [0059] All resulting samples were tested in the 300-cc batch hydrogenation reactor with pure H2 on a 7percent SAC solution at 2000 psi, 250° C. and 700 RPM. The rate of conversion of SAC to GBL and by-products was measured and reported as STY in Table 3. In the case of the Comparative Examples, the STY was corrected for the real weight of catalyst, which excluded the weight of the organics remaining in the sample after drying. Also, the STY of the Comparative Examples was corrected by subtracting the STY obtained from runs using catalyst and water.

With carbon monoxide; hydrogen in water

T=180°C; P=30003 Torr; 6 h;

Yu, Lei; Du, Xian-Long; Yuan, Jing; Liu, Yong-Mei; Cao, Yong; He, He-Yong; Fan, Kang-Nian

ChemSusChem, 2013 , vol. 6, # 1 p. 42 - 46 Title/Abstract

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With hydrogen in 1,4-dioxane

T=200°C; P=60006 Torr; 7 h; Inert atmosphereAutoclaveGlovebox; Hide Experimental Procedure

Kang, Ki Hyuk; Hong, Ung Gi; Bang, Yongju; Choi, Jung Ho; Kim, Jeong Kwon; Lee, Jong Kwon; Han, Seung Ju; Song, In Kyu

Applied Catalysis A: General, 2015 , vol. 490, p. 153 - 162 Title/Abstract

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Hydrogenation of succinic acid to BDO

Liquid-phase hydrogenation of succinic acid to BDO was con-ducted in a stainless steel autoclave reactor with a volume of200 ml. Prior to the reaction, the catalysts were reduced using anex situ reduction system at 500C for 4 h with a heating rate of5C/min under 5percent H2/N2flow (50 ml/min). In order to avoid airexposure, reduced catalyst (0.1 g), succinic acid (0.25 g), and 1,4dioxane (50 ml, an inert aprotic solvent) were charged into thereactor in an argon atmosphere glove box. The closed reactor filledwith argon was then mounted to the autoclave chamber as quicklyas possible. After purging the reactor with nitrogen, it was pressur-ized up to 50 bar using hydrogen. The sealed autoclave was heatedto the reaction temperature (200C), and then pressurized up to80 bar using hydrogen. Catalytic reaction was conducted with con-stant stirring (700 rpm) for 7 h. After the reaction, the reactor wascooled to room temperature and depressurized. Reaction productswere analyzed with a gas chromatograph (Younglin, ACME-6100)equipped with a flame ionization detector (FID). Conversion ofsuccinic acid, selectivity for product, and yield for product werecalculated according to the following equations.

With hydrogen in 1,4-dioxane

T=240°C; P=22502.3 - 45004.5 Torr; 4 h; Autoclave; Catalytic behavior; Reagent/catalyst;

You, Chenjia; Zhang, Chi; Chen, Lifang; Qi, Zhiwen

Applied Organometallic Chemistry, 2015 , vol. 29, # 10 p. 653 - 660 Title/Abstract

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With hydrogen in 1,4-dioxane

T=200°C; P=60006 Torr; 7 h; GloveboxInert atmosphereAutoclave; Catalytic behavior; Hide Experimental Procedure

Kang, Ki Hyuk; Hong, Ung Gi; Bang, Yongju; Choi, Jung Ho; Kim, Jeong Kwon; Lee, Jong Kwon; Han, Seung Ju; Song, In Kyu

Applied Catalysis A: General, 2015 , vol. 490, # 1 p. 153 - 162 Title/Abstract

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2.3. Hydrogenation of succinic acid to BDO

Liquid-phase hydrogenation of succinic acid to BDO was conducted in a stainless steel autoclave reactor with a volume of 200 ml. Prior to the reaction, the catalysts were reduced using an ex situ reduction system at 500 °C for 4 h with a heating rate of 5 °C/min under 5percent H2/N2 flow (50 ml/min). In order to avoid air exposure, reduced catalyst (0.1 g), succinic acid (0.25 g), and 1,4-dioxane (50 ml, an inert aprotic solvent) were charged into the reactor in an argon atmosphere glove box. The closed reactor filled with argon was then mounted to the autoclave chamber as quickly as possible. After purging the reactor with nitrogen, it was pressurized up to 50 bar using hydrogen. The sealed autoclave was heated to the reaction temperature (200 °C), and then pressurized up to 80 bar using hydrogen. Catalytic reaction was conducted with constant stirring (700 rpm) for 7 h. After the reaction, the reactor was cooled to room temperature and depressurized. Reaction products were analyzed with a gas chromatograph (Younglin, ACME-6100) equipped with a flame ionization detector (FID).

With hydrogen

T=200°C; P=37503.8 Torr; 20 h; Autoclave;

Liu, Xiaoran; Wang, Xicheng; Xu, Guoqiang; Liu, Qiang; Mu, Xindong; Liu, Haichao

Journal of Materials Chemistry A, 2015 , vol. 3, # 46 p. 23560 - 23569 Title/Abstract

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With C40H38NP3; hydrogen; [Ru(acac)3] in 2methyltetrahydrofuran

T=170°C; P=52505.3 Torr; 48 h;

Deng, Li; Kang, Bin; Englert, Ulli; Klankermayer, Jürgen; Palkovits, Regina

ChemSusChem, 2016 , vol. 9, # 2 p. 177 - 180 Title/Abstract

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With hydrogen in 1,4-dioxane

T=239.84°C; P=45004.5 Torr; 6 h; Catalytic behavior; Reagent/catalyst; Hide Experimental Procedure

Zhang, Chi; Chen, Lifang; Cheng, Hongye; Zhu, Xuedong; Qi, Zhiwen

Catalysis Today, 2016 , vol. 276, p. 55 - 61 Title/Abstract

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2.3. Catalytic evaluation of Pd/γAlOOH

The selective hydrogenation of SA to GBL was performed ina batch reactor (100 ml, Parr Corp.) at 513 K and 60 bar (H2). SA(0.4 g), reduced catalyst (0.2 g) and 1,4-dioxane (40 ml) as solventwere charged into the autoclave. Before heating, the reactor waspurged with hydrogen four times in order to remove air in theautoclave, and then pressurized up to 40 bar using hydrogen.

Afterheating the reactor to reaction temperature (513 K), hydrogen pres-sure was raised up to 60 bar. During the reaction, reaction mixturewas stirred at 500 rpm in order to avoid mass transfer limitation.The liquid samples taken from the autoclave at regular intervalswere analyzed by gas chromatograph and liquid chromatograph.For the gas chromatograph, a SE-54 column was used to separateproducts and a FID detector was used to identify GBL, THF and BDO.For the liquid chromatograph, an Inertsil®ODS-SP column (5 m4.6 × 150 mm) was used to identify SA, GBL, propionic acid (PA) andbutyric acid (BA).

A

B

52

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Al-Awadi, Nouria A.; Mathew, Tommy

International Journal of Chemical Kinetics, 1995 , vol. 27, # 9 p. 843 - 848 Title/Abstract

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T=499.9°C; var. temp., Ea; Rate constantThermodynamic data;

A

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C

D

E

F

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53

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With oxygen

T=69.9 - 229.9°C; flow and static experiments; isomerization reactions in oxygen; oxidation, isomerization and decomposition; effect of reaction vessel wall conditions; reaction mechanism; Product distributionRate constantThermodynamic data;

Heiss, Adolphe; Sahetchian, Krikor

International Journal of Chemical Kinetics, 1996 , vol. 28, # 7 p. 531 - 544 Title/Abstract

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54

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With diazomethane; potassium fluoride; dihydrogen peroxide

Yield given. Multistep reaction;

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Rx-ID: 4618459 Find similar reactions

Linker, Torsten; Maurer, Michael; Rebien, Frank

Tetrahedron Letters, 1996 , vol. 37, # 46 p. 8363 - 8366 Title/Abstract

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55

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60%

Hide Experimental Procedure

Rx-ID: 5406681 Find similar reactions

Kumar, Naresh; Read, Roger Wayne

Patent: US2004/110966 A1, 2004 ; Title/Abstract

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3,4-Dibromo-4-alkyl-5-(methylene)-2-tetrahydrofuranone

3,4-Dibromo-4-alkyl-5-(methylene)-2-tetrahydrofuranone Phosphorus pentoxide (11.4 g) was added with stirring to a solution of 2,3-dibromo-3-alkyl-4-oxopentanoic acid (4.6 g, 16.0 mmol) in dry dichloromethane (25 ml).

The mixture was heated at reflux with stirring for 2 h, and cooled to room temperature.

The resulting mixture was filtered through a pad of celite, washed with brine, dried over sodium sulfate and evaporated to yield the tetrahydrofuranone as a pale yellow oil (60-80percent).

With mineral acids; acetic acid

Kailan

Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1920 , vol. 94, p. 119 Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1922 , vol. 101, p. 89 Full Text Show Details

Henry

Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1892 , vol. 10, p. 113,116, 125, 126 Full Text Show Details

Fetizon,M. et al.

Tetrahedron, 1975 , vol. 31, p. 171 - 176 Full Text View citing articles Show Details

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Deslongchamps,P. et al.

Canadian Journal of Chemistry, 1975 , vol. 53, p. 2791 - 2807 Full Text View citing articles Show Details

Falbe,J. et al.

Chemische Berichte, 1965 , vol. 98, p. 886 - 893 Full Text View citing articles Show Details

Sucrow,W.; Klein,U.

Chemische Berichte, 1975 , vol. 108, p. 48 - 53 Full Text View citing articles Show Details

Matsuda,A.

Bulletin of the Chemical Society of Japan, 1969 , vol. 42, p. 2596 - 2599 Full Text View citing articles Show Details

Filliatre,C. et al.

Bulletin de la Societe Chimique de France, 1971 , p. 170 - 176 Full Text View citing articles Show Details

Barton,D.H.R. et al.

Journal of the Chemical Society, 1965 , p. 181 - 190 Full Text View citing articles Show Details

Renfrow,W.B. et al.

Journal of Organic Chemistry, 1961 , vol. 26, p. 935 - 937 Full Text View citing articles Show Details

Summerbell,R.K. et al.

Journal of Organic Chemistry, 1962 , vol. 27, p. 4433 - 4436 Full Text View citing articles Show Details

Ortiz,B. et al.

Journal of Organic Chemistry, 1972 , vol. 37, # 17 p. 2748 - 2750 Full Text View citing articles Show Details

Surzur,J.-M. et al.

Journal of Organic Chemistry, 1972 , vol. 37, # 17 p. 2782 - 2784 Full Text View citing articles Show Details

Meyers,A.I. et al.

Journal of Organic Chemistry, 1974 , vol. 39, p. 2783 - 2787 Full Text View citing articles Show Details

Bogatskii,A.V. et al.

Zhurnal Organicheskoi Khimii, 1971 , vol. 7, # 12 p. 2538 - 2544,2637 - 2642 Full Text View citing articles Show Details

Mills; Hodge

Carbohydrate Research, 1976 , vol. 51, p. 9,10-21 Full Text Show Details

Oda et al.

Journal of Organic Chemistry, 1961 , vol. 26, p. 1341 Full Text View citing articles Show Details

Heck

Journal of the American Chemical Society, 1963 , vol. 85, p. 1460,1463 Full Text Show Details

Denney; Smith

Journal of Organic Chemistry, 1962 , vol. 27, p. 3404,3406 Full Text Show Details

Stenberg; Perkin

Journal of Organic Chemistry, 1963 , vol. 28, p. 323 Full Text View citing articles Show Details

Fetizon et al.

Journal of Heterocyclic Chemistry, 1976 , vol. 13, p. 525 Full Text Show Details

Kuhnle et al.

Journal of the Chemical Society, Chemical Communications, 1972 , p. 287 Full Text View citing articles Show Details

Kamiya; Pukemura

Chemical and Pharmaceutical Bulletin, 1973 , vol. 21, p. 1401 Full Text Show Details

Batrakow; Bergel'son

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1965 , p. 348 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1965 , p. 369 Full Text Show Details

Juenge et al.

Journal of Organic Chemistry, 1966 , vol. 31, p. 3836 Full Text View citing articles Show Details

Daschunin et al.

J. Gen. Chem. USSR (Engl. Transl.), 1964 , vol. 34, p. 3096,3135 Full Text Show Details

Austin; Howard

Journal of the Chemical Society, 1961 , p. 3284 Full Text Show Details

Oka

Bulletin of the Chemical Society of Japan, 1961 , vol. 34, p. 12 Full Text Show Details

Oka

Bulletin of the Chemical Society of Japan, 1962 , vol. 35, p. 986,988 Full Text Show Details

Nikischin; Worob'ew

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1964 , p. 835 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1964 , p. 894 Full Text Show Details

Ethyl Corp.

Patent: US2986568 ; Chem.Abstr., 1962 , vol. 56, # 3420 Full Text Show Details

Kabalka et al.

Journal of Organic Chemistry, 1977 , vol. 42, p. 512,516 Full Text Show Details

Huson; McGill

South African Journal of Chemistry, 1978 , vol. 31, p. 91,92 Full Text Show Details

Glukhovtsev; Nikishin

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1976 , vol. 25, p. 2451 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1976 , vol. 25, p. 2633 Full Text View citing articles Show Details

Karpuschewa et al.

Izvestiya Sibirskogo Otdeleniya Akademii Nauk SSSR, 1971 , vol. 12, p. 110 Full Text Show Details

Shell

Patent: FR1319239 , 1963 ; Chem.Abstr., 1963 , vol. 59, # 8600c Full Text Show Details

Dale; Morgenlie

Acta Chemica Scandinavica (1947-1973), 1970 , vol. 24, p. 2408,2412,2415 Full Text Show Details

Fetizon et al.

Journal of the Chemical Society [Section] D: Chemical Communications, 1969 , p. 1118 Full Text View citing articles Show Details

Piancatelli et al.

Tetrahedron Letters, 1977 , p. 3483 Full Text View citing articles Show Details

Dittmer et al.

Chemistry and Industry (London, United Kingdom), 1964 , p. 152 Full Text Show Details

Bogdanova et al.

Doklady Chemistry, 1966 , vol. 167, p. 287 Doklady Akademii Nauk SSSR, 1966 , vol. 167, p. 95 Full Text Show Details

Nikishin et al.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1971 , Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1971 , vol. 20, p. 1842 Full Text View citing articles Show Details

Bailey; Johnson

Journal of Organic Chemistry, 1970 , vol. 35, p. 3574 Full Text View citing articles Show Details

Smissman et al.

Journal of Organic Chemistry, 1975 , vol. 40, p. 1640 Full Text View citing articles Show Details

Horton et al.

Journal of Organic Chemistry, 1969 , vol. 34, p. 3366,3367 Full Text Show Details

Ajinomoto

Patent: GB948242 , 1961 ; Chem.Abstr., 1964 , vol. 60, # 11903h Full Text Show Details

Juenge et al.

Tetrahedron, 1971 , vol. 27, p. 2671 Full Text View citing articles Show Details

Nikishin et al.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1973 , Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1973 , vol. 22, p. 825 Full Text View citing articles Show Details

Heyns; Buchholz

Chemische Berichte, 1976 , vol. 109, p. 3707,3713, 3725 Full Text Show Details

Collman et al.

Journal of the American Chemical Society, 1976 , vol. 98, p. 4685 Full Text View citing articles Show Details

Lukeha.t; Zeile

Journal of Organometallic Chemistry, 1975 , vol. 97, p. 421,423, 425 Full Text View citing articles Show Details

Kabalka

Organic Preparations and Procedures International, 1977 , vol. 9, p. 133,140 Full Text Show Details

Clark; Emsley

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1975 , p. 2129 Full Text Show Details

Ogibin et al.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1974 , Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1974 , vol. 23, p. 2522 Full Text Show Details

Beckwith; Goodrich

Australian Journal of Chemistry, 1965 , vol. 18, p. 747,754 Full Text Show Details

Cassebaum

Pharmazie, 1960 , vol. 15, p. 310,312 Full Text Show Details

Nikishin et al.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1976 , Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1976 , vol. 25, p. 2630 Full Text View citing articles Show Details

Mistrik; Durmis

Chemicke Zvesti, 1969 , vol. 23, p. 286,287, 291 Full Text Show Details

Deno; Potter

Journal of the American Chemical Society, 1967 , vol. 89, p. 3550,3551, 3552 Full Text View citing articles Show Details

Hide Experimental Procedure

Specific compounds of interest within Formula I are the following: 7α-acetylthio-3-oxo-4,15-androstadiene-[17(β-1 ')-spiro-5']perhydrofuran-2'-one; 3-oxo-7α-propionylthio-4,15-androstadiene-[17((β-1')-spiro-5']perhydrofuran-2'-one; 6β,7β-methylene-3-oxo-4,15-androstadiene-[17((β-1 ')-spiro-5']perhydrofuran-2'-one;

Jacobson; Mares; Zambri

Journal of the American Chemical Society, 1979 , vol. 101, # 23 p. 6938 - 6946 Title/Abstract

Full Text View citing articles Show Details

Ivanskii; Dolgov

Kinetics and Catalysis, 1963 , vol. 4, p. 138 p. 165 Full Text Show Details

Francke; Bruemmer

Planta Medica, 1978 , vol. 34, p. 332,333 Full Text Show Details

Keller, Bradley T.; McMahon, Ellen G.

Patent: US2003/219401 A1, 2003 ; Title/Abstract

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vol. 20, p. 1742

vol. 22, p. 801

vol. 23, p. 2430,2433

vol. 25, p. 2448

15α,16α-methylene-3-oxo-4,7α-propionylthio-4-androstene[17(β-1 ')-spiro-5']perhydrofuran-2'-one; 6β,7β,15α,16α-dimethylene-3-oxo-4-androstene[17(β-1 ')-spiro-5']-perhydrofuran-2'-one; 7α-acetylthio-15β,16β-Methylene-3-oxo-4-androstene-[17(β-1 ')-spiro-5']perhydrofuran-2'-one; 15β,16β-methylene-3-oxo-7β-propionylthio-4-androstene-[17(β-1')-spiro-5']perhydrofuran-2'-one; and 6β,7β,15β,16β-dimethylene-3-oxo-4-androstene-[17(β-11 ')-spiro-5']perhydrofuran-2'-one.

Ayerst, McKenna and Harrison Limited

Patent: US4171443 A1, 1979 ;

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Title/Abstract

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4:3-[(Dimethylamino)methyl]-1,2,3,3a,5,6-hexahydro-3a-methyl-4-oxa-10b-azafluoranthene (I; R1 =H, R2 =CH3, R3 =CH2 N(CH3)2 and X=O)

Similarly, replacing 3-acetyldihydro-2(3H)-furanone in Example 1 with an equivalent amount of 3-propionyldihydro-2(3H)furanone, 3-pentionyldihydro-2(3H)-furanone or 3-(4-methylpentionyl)dihydro-2(3H) furanone and following the procedures of Examples 1 to 4, the following compounds of formula I are obtained respectively: 3-[(dimethylamino)methyl]-1,2,3,3a,5,6-hexahydro-3aethyl-4-oxa-10b-azafluoranthene, 3-[(dimethylamino)methyl]-1,2,3,3a,5,6-hexahydro-3a-butyl-4-oxa-10b-azafluoranthene and 3-[(dimethylamino)methyl]-1,2,3,3a,5,6-hexahydro-3a-(3-methylbutyl)-4-oxa-10b-azafluoranthene.

Kumar, Naresh; Read, Roger Wayne

Patent: US2004/110966 A1, 2004 ;

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Title/Abstract

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Synthesis of 4-bromo-5-(bromomethylene)-2-tetrahydrofuranone

Synthesis of 4-bromo-5-(bromomethylene)-2-tetrahydrofuranone Phosphorus pentoxide (22.5 g) was added with stirring to a solution of 3,5-dibromo-4-oxopentanoic acid (30.4 g, 0.11 mol) in dry dichloromethane (500 ml).

The mixture was heated at reflux with stirring for 2 h, and cooled to room temperature.

The resulting mixture was filtered through a pad of filter aid, washed with brine, dried over sodium sulfate and evaporated to yield the tetrahydrofuranone (mixture of Z- and E-isomers in 4:1 ratio) as a pale yellow oil (23.4 g, 82percent).

The oil solidified on standing at room temperature overnight.

Crystallisation from dichloromethane/light petroleum (60-80° C.) gave an analytically pure sample of the Z-isomer. m p. 79° C. νmax3094, 3027, 2947, 1799, 1634, 1393, 1289, 1114, 949, 838, 747, 718, 660 cm-1. λmax279 nm (ε 4938).

56

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With potassium hydroxide

Carriere

Annales de Chimie (Cachan, France), 1922 , vol. <9> 17, p. 122 Full Text Show Details

57

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With hydrogen

T=230 - 250°C; durch Leiten ueber einen Kupfer-BimssteinKatalysator;

Fiat Final Report

Nr. 945, S. 2 Full Text Show Details

I.G. Farbenind.

Patent: DE699945 ;

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I.G. Farbenind.

Patent: IT374925 ; Full Text Show Details

58

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Wojcik; Adkins

Journal of the American Chemical Society, 1933 , vol. 55, p. 4943 Full Text Show Details

T=250°C; P=220652 Torr; Hydrogenation;

59

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With iodine

T=150°C;

Rx-ID: 5406685 Find similar reactions

Sircar

Journal of the Chemical Society, 1928 , p. 901 Full Text View citing articles Show Details

Windaus; Klaenhardt

Chemische Berichte, 1921 , vol. 54, p. 585 Full Text View citing articles Show Details

60

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Eijkman

Chem. Zentralbl., 1907 , vol. 78, # I p. 1617 Full Text Show Details

61

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Imp.Chem.Ind.

Patent: US2463776 , 1947 ;

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62

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Berkowitz; Rylander

Journal of the American Chemical Society, 1958 , vol. 80, p. 6682 Full Text View citing articles Show Details

63

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Behandeln mit Salzsaeure;

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Fichter; Herbrand

Chemische Berichte, 1896 , vol. 29, p. 1193 Full Text View citing articles Show Details

64

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Schlesinger; Brown

Patent: US2683721 , 1952 ;

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65

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With sodium amalgam; acetic acid

Perkin; Sprankling

Journal of the Chemical Society, 1899 , vol. 75, p. 17 Full Text View citing articles Show Details

Carriere

Annales de Chimie (Cachan, France), 1922 , vol. <9> 17, p. 122 Full Text Show Details

A

B

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66

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T=100 - 200°C;

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Reppe et al.

Justus Liebigs Annalen der Chemie, 1955 , vol. 596, p. 1,162,182 Full Text View citing articles Show Details

67

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Buckley; Levy

Journal of the Chemical Society, 1951 , p. 3016 Full Text View citing articles Show Details

T=300°C; P=228000 Torr;

68

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Chaikin; Brown

Journal of the American Chemical Society, 1949 , vol. 71, p. 124 Full Text Show Details

zuletzt auf dem Dampfbad;

69

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Perkin; Sprankling

Journal of the Chemical Society, 1899 , vol. 75, p. 17 Full Text View citing articles Show Details

A

B

70

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I.G.Farbenind.

Patent: DE699945 , 1938 ; DRP/DRBP Org.Chem.

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Reppe et al.

Justus Liebigs Annalen der Chemie, 1955 , vol. 596, p. 162,182 Full Text Show Details

T=120 - 150°C;

A

B

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71

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I.G.Farbenind.

Patent: DE699945 , 1938 ; DRP/DRBP Org.Chem.

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Reppe et al.

Justus Liebigs Annalen der Chemie, 1955 , vol. 596, p. 162,182 Full Text Show Details

T=120 - 150°C;

A

B

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72

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I.G.Farbenind.

Patent: DE699945 , 1938 ; DRP/DRBP Org.Chem.

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Reppe et al.

Justus Liebigs Annalen der Chemie, 1955 , vol. 596, p. 162,182 Full Text Show Details

T=250°C;

A

B

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73

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Destillation;

Fittig; Chanlarow

Justus Liebigs Annalen der Chemie, 1884 , vol. 226, p. 331,332 Full Text View citing articles Show Details

T=5°C; Einfluss von Mineralsalzen auf das Gleichgewicht;

Long et al.

Journal of Physical Chemistry, 1951 , vol. 55, p. 823-828,829 Full Text Show Details

T=25°C; Einfluss von Mineralsalzen auf das Gleichgewicht;

Long et al.

Journal of Physical Chemistry, 1951 , vol. 55, p. 823-828,829 Full Text Show Details

A

B

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74

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T=25°C; Equilibrium constant;

Coffin; Long

Journal of the American Chemical Society, 1952 , vol. 74, p. 5767 Full Text View citing articles Show Details

T=39°C; Equilibrium constant;

Coffin; Long

Journal of the American Chemical Society, 1952 , vol. 74, p. 5767 Full Text View citing articles Show Details

Coffin; Long

Journal of the American Chemical Society, 1952 , vol. 74, p. 5767 Full Text View citing articles Show Details

T=50°C; Equilibrium constant;

A

B

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75

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Long et al.

Journal of Physical Chemistry, 1951 , vol. 55, p. 823-828,829 Full Text Show Details

T=0°C; Equilibrium constant;

A

B

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76

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T=25°C; Equilibrium constant;

Long et al.

Journal of Physical Chemistry, 1951 , vol. 55, p. 823-828,829 Full Text Show Details

T=5°C; Equilibrium constant;

Long et al.

Journal of Physical Chemistry, 1951 , vol. 55, p. 823-828,829 Full Text Show Details

A

77

B

C

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Fittig; Roeder

Justus Liebigs Annalen der Chemie, 1885 , vol. 227, p. 19 Full Text Show Details

Autenrieth

Chemische Berichte, 1905 , vol. 38, p. 2550 Full Text Show Details

bei der trocknen Destillation;

78

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Pimenta; Bayona; Garcia; Solanas

Archives of Environmental Contamination and Toxicology, 2000 , vol. 38, # 2 p. 169 - 175 Title/Abstract

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Decomposition; Formation of xenobioticspyrolysis;

79

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With sodium dihydrogenphosphate; sodium perchlorate; sodium nitrite

T=24.84°C; pH=3.14; Kinetics; Further Variations:pH-values;

Garcia-Santos; Calle; Casado

Journal of the American Chemical Society, 2001 , vol. 123, # 31 p. 7506 - 7510 Title/Abstract

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With sodium dihydrogenphosphate; sodium perchlorate; sodium nitrite

T=25°C; pH=3.14;

Garcia-Santos; Calle; Casado

Journal of the American Chemical Society, 2001 , vol. 123, # 31 p. 7506 - 7510 Title/Abstract

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A

B

80

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A: 96.5% B: 99.4%

With hydrogen; Cu-based catalyst

T=210°C; reaction in vapour phase, fixed bed reactor, coupled dehydrogenation reactions of title comp. and INO 160; Product distribution; Further Variations:Temperatures;

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Zhu, Yu-Lei; Xiang, Hong-Wei; Li, Yong-Wang; Jiao, Haijun; Wu, Gui-Sheng; Zhong, Bing; Guo, Guang-Qing

New Journal of Chemistry, 2003 , vol. 27, # 2 p. 208 - 210 Title/Abstract

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A

B

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81

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A: 98.8% B: 0.8%

With hydrogen; Cu-based catalyst

T=190°C; reaction in vapour phase, fixed bed reactor; Product distribution; Further Variations:Temperatures;

Zhu, Yu-Lei; Xiang, Hong-Wei; Li, Yong-Wang; Jiao, Haijun; Wu, Gui-Sheng; Zhong, Bing; Guo, Guang-Qing

New Journal of Chemistry, 2003 , vol. 27, # 2 p. 208 - 210 Title/Abstract

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82

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0.83 mmol

With lead(IV) acetate; ammonium chloride in acetic acid

T=80°C; 0.3 h;

Nikishin, Gennady I.; Sokova, Lyubov L.; Makhaev, Viktor D.; Kapustina, Nadezhda I.

Mendeleev Communications, 2003 , vol. 13, # 6 p. 264 - 265 Title/Abstract

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0.95 mmol

With lead(IV) acetate; ammonium chloride

T=20°C; 6 h; mechanical activation;

Nikishin; Sokova; Chizhov; Makhaev; Kapustina

Russian Chemical Bulletin, 2004 , vol. 53, # 10 p. 2200 - 2204

Title/Abstract

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83

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74 % Chromat.

With ruthenium(IV) oxide; Oxonereg;; sodium hydrogencarbonate in water; ethyl acetate; acetonitrile

T=20°C; 1 h;

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Yang, Dan; Chen, Fei; Dong, Ze-Min; Zhang, Dan-Wei

Journal of Organic Chemistry, 2004 , vol. 69, # 6 p. 2221 - 2223 Title/Abstract

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84

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99%

With hydrogen in methanol

P=26252.6 Torr; 2 h; Autoclave; Reagent/catalyst; Hide Experimental Procedure

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Tsinghua University; Wang, Tiefeng; Li, Xiaodan; Lan, Xiaocheng; Lu, Shuting

Patent: CN105254599 A, 2016 ; Location in patent: Paragraph 0051; 0052 ; Title/Abstract

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7:Example 7

Furanone Catalytic Hydrogenation: The 0.6g Pd0.5 / SiO2 catalyst, 6.0g2 (5H) - furanone, 100ml methanol was added to the autoclave, purged with hydrogen and 0.5 hours, warmed to 80 deg.] C, the hydrogen pressurized to 3.5MPa, hydrogen a flow rate of 180ml / min, stirring 800rmp, after 1.5 hours the reaction yield γ- butyrolactone99percent.

92.6%

With 0.5 palladium on silica gel; hydrogen in methanol

T=80°C; P=26252.6 Torr; Autoclave; Catalytic behaviorKinetics; Reagent/catalyst;

Li, Xiaodan; Lan, Xiaocheng; Wang, Tiefeng

Green Chemistry, 2016 , vol. 18, # 3 p. 638 - 642 Title/Abstract

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With 1,4-dihydronicotinamide adenine dinucleotide; sodium phosphate buffer; Marchantia polymorpha p68 reductase

T=35°C; pH=7.0; 4 h;

Shimoda, Kei; Kubota, Naoji

Tetrahedron Asymmetry, 2004 , vol. 15, # 24 p. 3827 - 3829 Title/Abstract

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Hide Details

55 %Spectr.

With palladium 10 on activated carbon; hydrogen

T=20°C; P=12929 Torr; 6 h;

Shiramizu, Mika; Toste, F. Dean

Angewandte Chemie - International Edition, 2013 , vol. 52, # 49 p. 12905 - 12909 Angew. Chem., 2013 , vol. 125, # 49 p. 13143 - 13147,5 Title/Abstract

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With Old Yellow Enzyme 1; NADH in dimethyl sulfoxide

T=30°C; 24 h; Enzymatic reaction; Reagent/catalystSolvent;

Turrini, Nikolaus G.; Hall, Mlanie; Faber, Kurt

Advanced Synthesis and Catalysis, 2015 , vol. 357, # 8 p. 1861 - 1871 Title/Abstract

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85

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81%

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Stage #1: With water; triethylamine; dicarbonylacetylacetonato rhodium (I) in 1,4-dioxane

T=20 - 120°C; P=2700.27 - 186019 Torr; 2 h; Stage #2: With hydrogen

T=20 - 200°C; P=37503.8 - 150015 Torr; 1 h; Hide Experimental Procedure

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BASF Aktiengesellschaft

Patent: US6346629 B1, 2002 ; Location in patent: Page column 6 ; Title/Abstract

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3:Example 2

The initial charge was 672 mg (2.6 mmol) of Rh(CO)2acac, 2.25 g (22.3 mmol) of triethylamine and 32.8 g (1.8 mol) of water in 400 ml of dioxane. 8.2 l (0.31 mol) of acetylene were injected at room temperature with stirring to a pressure of 3.6 bar. The pressure was then raised to 200 bar with carbon monoxide. The reaction batch was heated to 120° C., raising the pressure to 248 bar, and subsequently stirred for 2 h. After cooling and reactor decompression, a sample was taken and analyzed by gas chromatography using the technique of the internal standard. Based on the amount of acetylene used, 59percent of 2(5H)-furanone and 24percent of butyrolactone had formed. 50 bar of hydrogen were then injected at room temperature and the reaction batch heated to 200° C. in the autoclave, raising the pressure to 89 bar. The pressure was then raised to 200 bar with hydrogen, which was followed by 1 h of stirring. After cooling and autoclave decompression the autoclave's effluent was filtered. The filtrate was found to contain only 1percent of the rhodium used. The solid filter residue was reusable as catalyst. Following a distillative workup, butyrolactone was isolated in a yield of 81percent, based on the amount of acetylene used.

78%

Stage #1: With water; triethylamine; dicarbonylacetylacetonato rhodium (I) in 1,4-dioxane

T=20 - 120°C; P=2700.27 - 186019 Torr; 2 h; Stage #2: With hydrogen

T=20 - 200°C; P=37503.8 - 150015 Torr; 1 h; Hide Experimental Procedure

BASF Aktiengesellschaft

Patent: US6346629 B1, 2002 ; Location in patent: Page column 6-7 ; Title/Abstract

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3:Example 3

Example 2 was repeated, except that the hydrogenation reaction effluent was centrifuged. The centrifugate was worked up by distillation. The solid removed was introduced as an initial charge in 400 ml of dioxane and admixed with 2.25 g (22.3 mmol) of triethylamine and 32.8 g (1.8 mol) of water. 8.2 l (0.31 mol) of acetylene were injected at room temperature with stirring to a pressure of 3.6 bar. The pressure was then raised to 200 bar with carbon monoxide. The reaction batch was heated to 120° C., raising the pressure to 248 bar, and subsequently stirred for 2 h. After cooling and reactor decompression a sample was taken and analyzed by gas chromatography using the technique of the internal standard. 50 bar of hydrogen were then injected at room temperature and the reaction batch heated to 200° C. in the autoclave, raising the pressure to 89 bar. The pressure was then raised to 200 bar with hydrogen, which was followed by 1 h of stirring. After cooling and autoclave decompression the autoclave's effluent was again centrifuged to remove and reuse the catalyst. The centrifugate was worked up by distillation. The sequence of carbonylation/hydrogenation/catalyst removal/carbonylation was repeated altogether five times without addition of fresh catalyst. The distillative yields of butyrolactone obtained after each cycle, in each case based on the amount of acetylene used, are recited in Table 2 below: A

B

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86

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Rx-ID: 22826980 Find similar reactions

A: 22% B: 52%

With water; triethylamine; dicarbonylacetylacetonato rhodium (I) in 1,4-dioxane

T=20 - 120°C; P=2700.27 - 186019 Torr; 2 h; Hide Experimental Procedure

BASF Aktiengesellschaft

Patent: US6346629 B1, 2002 ; Location in patent: Page column 5 ; Title/Abstract

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1:Example 1

The initial charge was 672 mg (2.6 mmol) of Rh(CO)2acac, 2.25 g (22.3 mmol) of triethylamine and 32.8 g (1.8 mol) of water in 400 ml of dioxane. 8.2 l (0.31 mol) of acetylene were injected at room temperature with stirring to a pressure of 3.6 bar. The pressure was then raised to 200 bar with carbon monoxide. The reaction batch was heated to 120° C., raising the pressure to 248 bar, and subsequently stirred for 2 h. After cooling and reactor decompression, the effluent was worked up by distillation. Based on the amount of acetylene used, 52percent of 2(5H)-furanone and 22percent of butyrolactone had formed. The bottom product of the distillation, which contained the catalyst, was introduced as an initial charge in 400 ml of dioxane and admixed with 2.25 g (22.3 mmol) of triethylamine and 32.8 g (1.8 mol) of water. 8.2 l (0.31 mol) of acetylene were injected at room temperature to a pressure of 3.6 bar. The pressure was then raised to 200 bar with carbon monoxide. The reaction batch was heated to 120° C., raising the pressure to 248 bar, and subsequently stirred for 2 h. After cooling and reactor decompression, the reactor's effluent was worked up by distillation and the bottom product of the distillation, which contained the catalyst, reused. Altogether this procedure was repeated three times without addition of fresh catalyst. The respective yields of product of value (reported as the sum total of 2(5H)-furanone and butyrolactone) are shown in Table 1.

With water; triethylamine; dicarbonylacetylacetonato rhodium (I) in 1,4-dioxane

T=20 - 120°C; P=2700.27 - 186019 Torr; 2 h; Hide Experimental Procedure

BASF Aktiengesellschaft

Patent: US6346629 B1, 2002 ; Location in patent: Page column 5 ; Title/Abstract

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1:Example 1

The initial charge was 672 mg (2.6 mmol) of Rh(CO)2acac, 2.25 g (22.3 mmol) of triethylamine and 32.8 g (1.8 mol) of water in 400 ml of dioxane. 8.2 l (0.31 mol) of acetylene were injected at room temperature with stirring to a pressure of 3.6 bar. The pressure was then raised to 200 bar with carbon monoxide. The reaction batch was heated to 120° C., raising the pressure to 248 bar, and subsequently stirred for 2 h. After cooling and reactor decompression, the effluent was worked up by distillation. Based on the amount of acetylene used, 52percent of 2(5H)-furanone and 22percent of butyrolactone had formed. The bottom product of the distillation, which contained the catalyst, was introduced as an initial charge in 400 ml of dioxane and admixed with 2.25 g (22.3 mmol) of triethylamine and 32.8 g (1.8 mol) of water. 8.2 l (0.31 mol) of acetylene were injected at room temperature to a pressure of 3.6 bar. The pressure was then raised to 200 bar with carbon monoxide. The reaction batch was heated to 120° C., raising the pressure to 248 bar, and subsequently stirred for 2 h. After cooling and reactor decompression, the reactor's effluent was worked up by distillation and the bottom product of the distillation, which contained the catalyst, reused. Altogether this procedure was repeated three times without addition of fresh catalyst. The respective yields of product of value (reported as the sum total of 2(5H)-furanone and butyrolactone) are shown in Table 1.

87

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Rx-ID: 22845720 Find similar reactions

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With oxygen

T=250°C; P=3750.38 Torr; 0.333333 h; Compressed gas(es);

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Haldor Topsoe A/S

Patent: EP1167361 A2, 2002 ; Location in patent: Page 4 ; Title/Abstract

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Haldor Topsoe A/S

Patent: EP1167361 A2, 2002 ; Location in patent: Page 4 ;

With oxygen; Mn2O3

Title/Abstract

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With oxygen

Haldor Topsoe A/S

Patent: EP1167361 A2, 2002 ; Location in patent: Page 4 ;

Title/Abstract

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A

B

C

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88

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Rx-ID: 22873752 Find similar reactions

A: 1.05% B: 2.39% C: 2.46%

With catalyst B

T=360°C; 2 - 30.17 h;

A: 0.58% B: 0.74% C: 0.41%

With catalyst A

T=360°C; 2 - 24 h;

EASTMAN CHEMICAL COMPANY

Patent: WO2002/6198 A2, 2002 ; Location in patent: Table V ; Title/Abstract

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EASTMAN CHEMICAL COMPANY

Patent: WO2002/6198 A2, 2002 ; Location in patent: Table IV ; Title/Abstract

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A

B

C

D

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89

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With hydrogen in water

T=200 - 250°C; P=46544.6 Torr; 229 h; Product distribution / selectivity; Hide Experimental Procedure

DAVY PROCESS TECHNOLOGY LIMITED

Patent: WO2005/51875 A1, 2005 ; Location in patent: Page/Page column 13-14 ; Title/Abstract

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4:

Example 4 illustrates that the catalysis may be performed on a continuous basis. The continuous reactor consisted of an 800 ml Hastelloy Reactor equipped with a Parr Magana drive, gas induction stirrer, baffles and thermowell. Hydrogen (stripping gas) was supplied to the reactor via a Bronkhorst mass thermal flow controller. Nitrogen was regulated down to the desired pressure and supplied to the reactor, when required via a needle valve. 30wtpercent maleic acid solution and deionised water were supplied to the reactor via two concept PUIII constametric pumps. During operation the maleic acid solution was added at a constant rate whilst the deionised water was added only to maintain the level in the reactor. The level in the reactor was monitored by the difference in temperature was then processed using a Moore's 351 controller to drive the deionised water constametric pump. Excess gas to that required in the reaction was added and the excess removed with the volatile products via a heated transfer line. The volatile products condensed in a condenser and were collected in a catch pot. The excess gas was vented through a backpressure regulator. Ruthenium (III) acetylacetonate (0. 91mmols 0.3606g) and tris-l, l, l- (diphenyl- phosphinomethyl) ethane (l. lmmols, 0.7081g), 156.9 were transferred into the reactor. This was sealed, purged with nitrogen before being pressurised to 900psig with nitrogen and this was set as the set point for the back pressure regulator, the stirrer started at 1000rpm and the reactor was heated to 200°C. Once 200° was reached the reactor was left for 30 minutes. 150g of 30wtpercent maleic acid solution was pumped into the reactor and the water pump was turned on to maintain the level in the reactor and the hydrogen flow started at 100NLPH. After a further hour the temperature of the reactor was increased to 250°C. Maleic acid solution was fed into the reactor at an initial rate of 0. 5mls/minute. After 228 hours on line a total of 7126g of maleic acid and water had been fed and 6739g of product recovered giving an overall mass balance of 95percent. This was bulked and analysed, the water and organic analysis was determined using an HP gas chromatograph equipped with a micro TCD (wtpercent) water (89.17), propanol (0.17), tetrahydrofuran (4.33), propionic acid (0.52) ; y-butyrolactone (5.79) others (0.02), giving an overall molar selectivity to tetrahydrofuran of 34percent, and to y-butyrolactone of 59percent.

A

B

C

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90

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A: 62.2- 93.5 %Chromat.

With hydrogen

T=253 - 257°C; P=3750.38 - 7500.75 Torr; Gas phase; Product distribution / selectivity;

BASF Aktiengesellschaft

Patent: WO2005/58853 A2, 2005 ; Location in patent: Page/Page column 18-19 ;

B: 0.2 33.9 %Chromat.

C: 2.6 5.2 %Chromat.

A: 53.4 53.6 %Chromat.

B: 42.8 43.9 %Chromat.

C: 1.1 2.1 %Chromat.

With hydrogen

T=245 - 246°C; P=6750.68 Torr; 1226 - 3081 h; Gas phase; Product distribution / selectivity;

Title/Abstract

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BASF Aktiengesellschaft

Patent: WO2005/58853 A2, 2005 ; Location in patent: Page/Page column 19-20 ; Title/Abstract

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91

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43%

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Rx-ID: 24064772 Find similar reactions

in 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4Hpyran; ethyl acetate

Li, Leping; Chen, Xiaoqi; Fan, Pingchen; Mihalic, Jeffrey Thomas; Cutler, Serena

Patent: US2002/45749 A1, 2002 ;

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Title/Abstract

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126.b:Example 126

Step b.

This intermediate (0.075 g, 0.3 mmol) was heated with triphosgene (0.300 g, 1 mmol) in DCM (2 mL) to 80° C. in a sealed vial for 2 hrs.

It was then cooled to rt, poured into water and extracted with EtOAc. The organic layer was separated, washed with brine, dried with anhydrous Na2SO4, concentrated by rotary evaporation and purified by flash chromatography on silica gel with a gradient elution of 30-70percent EtOAc/hexanes to afford the corresponding oxolidinone as a white solid (0.036 g, 43percent).

A

B

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92

B: 82%

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Rx-ID: 25858202 Find similar reactions

Kumar, Naresh; Read, Roger Wayne

Patent: US2004/110966 A1, 2004 ; Title/Abstract

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Synthesis of 4-bromo-3-butyl-5-(dibromomethylene)-2-tetrahydrofuranone

Synthesis of 4-bromo-3-butyl-5-(dibromomethylene)-2-tetrahydrofuranone Phosphorus pentoxide (10.0 g) was added with stirring to a solution of 2-(1,3,3-tribromo-2-oxopropyl)hexanoic acid (7.7 g, 0.11 mol) in dry dichloromethane (150 ml).

The mixture was heated at reflux with stirring for 2 h, and cooled to room temperature.

The resulting mixture was filtered through a pad of filter aid, washed with brine, dried over sodium sulfate and evaporated to yield the tetrahydrofuranone as a pale brown oil (7.0 g, 82percent) that solidified on standing at 4° C. overnight. νmax2958, 2930, 2871, 1820, 1782, 1638, 1455, 1127, 1086, 965, 849, 757, 718 cm-1. 1H n.m.r. δ (CDCl3) 0.93, t, J 6.7 Hz, (H4')3; 1.37-1.81, m, (H3')2-(H1')2; 3.22, t, J 7.5 Hz, H3; 4.79, s, H4. 13C n.m.r. δ (CDCl3): 14.1, C4'; 22.5, C3'; 28.9, C1'; 31.6, C2'; 43.6, C4; 53.7, C3; 76.5, 5-CBr2; 149.8, C5; 172.5, C2.

A

B

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93

Synthesize Find similar Rx-ID: 28426692 Find similar reactions

A: 4.8% B: 2.5%

With hydrogen; 3 Sn/7 Pt on C

T=120°C; P=150015 Torr; 24 h; Product distribution / selectivity; Hide Experimental Procedure

Bauduin, Christophe; Fischer, Wolfgang; Pinkos, Rolf; Scholten, Edzard

Patent: US2009/137825 A1, 2009 ; Location in patent: Page/Page column 7-8 ; Title/Abstract

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1:

Reference Example 1Experiments on the Direct Catalytic Hydrogenation of Succinic Salts to THFFor comparative purposes, various salts of succinic acid were subjected to a homogeneous or heterogeneous hydrogenation. Either no reaction (disodium salt) or the formation of various hydrogenation products, such as BDO, GBL or pyrrolidone, is observed, but not the formation of the desired THF product.; Heterogeneous hydrogenation conditions: 3percent Sn/7percent Pt on C, 120° C., 200 bar H2, 24 h.; (b)The monosodium salt can be regarded as a 50:50 mixture of diacid and disodium salt. Only the diacid could in butanediol BDO and GBL. No conversion of a sodium carboxylate was observed.

A

B

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94

Synthesize Rx-ID: 28984929 Find similar reactions

Tosoh F-Tech, Inc.

Patent: EP1403238 A1, 2004 ; Location in patent: Page 4 ; Title/Abstract

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95

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29 %Spectr.

With cyclohexa-1,4-diene in benzene-d6

T=135°C; 48 h; Inert atmosphere;

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Rx-ID: 29149637 Find similar reactions

Baroudi, Abdulkader; Mauldin, Justin; Alabugin, Igor V.

Journal of the American Chemical Society, 2010 , vol. 132, # 3 p. 967 - 979 Title/Abstract

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96

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44 %Spectr.

With cyclohexa-1,4-diene in benzene-d6

T=135°C; 72 h; Inert atmosphere;

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Rx-ID: 29149641 Find similar reactions

Baroudi, Abdulkader; Mauldin, Justin; Alabugin, Igor V.

Journal of the American Chemical Society, 2010 , vol. 132, # 3 p. 967 - 979 Title/Abstract

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97

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With 5 wt Ru/carbon; hydrogen in water

T=125 - 175°C;

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Rx-ID: 29348337 Find similar reactions

Vispute, Tushar P.; Huber, George W.

Green Chemistry, 2009 , vol. 11, # 9 p. 1433 - 1445 Title/Abstract

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98

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40 %Spectr.

With carbonylchlorohydridetris(triphenylphosphine) ruthenium(II) in toluene

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Omura, Sohei; Fukuyama, Takahide; Murakami, Yuji; Okamoto, Hiromi; Ryu, Ilhyong

Chemical Communications, 2009 , # 44 p. 6741 - 6743

T=110°C; 5 h; Inert atmosphere;

Title/Abstract

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A

B

C

D

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99

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A: 20.7% B: 22.6% C: 15% D: 20.2%

With ZnCuO2; hydrogen

T=260°C; P=750.075 Torr;

Ding, Guoqiang; Zhu, Yulei; Zheng, Hongyan; Zhang, Wei; Li, Yongwang

Catalysis Communications, 2010 , vol. 11, # 14 p. 1120 - 1124 Title/Abstract

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