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

Reaxys

PubChem

eMolecules

Reactions (367)

Yield

Substances (27)

Citations (530)

Conditions

References A

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298

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A: 0.45% B: 0.06% C: 0% D: 0.21% E: 0.36% F: 98.73% G: 0.04% H: 0.08%

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 11-13 ;

With hydrogen; 0.5percent Pd on Rutile TiO2

T=110°C; Product distribution / selectivity; Hide Experimental Procedure

Title/Abstract Full Text Show Details

The catalyst testing unit is comprised of a two-reactor system connected in series where maleic acid is first converted to succinic acid (SAC) in the first reactor at about 110° C. The effluent from the first stage reactor is delivered to the second stage reactor for the conversion of succinic acid to mainly BDO. Operating pressure is at 2500 to 4000 psi and internal reactor temperature is initially set at 165° C. Thereafter, temperature is adjusted closer to the temperature where a high conversion of SAC (about 99.7percent) is obtained. This temperature generally may vary from about 130° C. to about 175° C. At the lower end of the temperature range BDO selectivity is higher (80percent or higher) whereas THF is favored at higher temperatures (over 5percent). The results of the activity evaluation of a catalysts made according to the procedure of catalyst Example 1(a) is shown in Table 1a. Activity evaluation of a catalyst made according to the procedure of catalyst Example 2 is shown in Table 1(b). Catalyst results of the activity evaluation of a catalysts made according to the procedure of catalyst Example 3 is shown in Table 1(c).Tables 1a, 1b and 1c show that catalysts of Example 1(a), comprising Pd/Re on a rutile titanium dioxide support, and catalysts of Example 2 and Example 3, comprising Pd on a rutile titanium dioxide support, completely convert maleic acid to succinic acid with high selectivity to succinic acid and low amounts of other by-products. The Catalyst Testing Unit (CTU) results for Catalyst Example 1 and Catalyst Example 2 show that (a) Both 1/16 inch and inch Rutile extrudates can be used for hydrogenation. For carbon, inch was found to be less effective. (b) For maleic to succinic hydrogenation there is no need for other co-catalysts such as Ag, Fe, Na, etc., (c) 0.5percent Pd alone on a rutile TiO2 support gives good conversion of maleic acid to succinic acid. A

299

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Rx-ID: 28849397 Find similar reactions

A: 78% B: 75%

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Das, Arindam; Chaudhuri, Rupsha; Liu, Rai-Shung

Chemical Communications, 2009 , # 27 p. 4046 - 4048 Title/Abstract Full Text View citing articles Show Details

With silver hexafluoroantimonate; PPh3 gold(I) chloro complex; oxygen

T=25°C;

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300

Synthesize Find similar Rx-ID: 2124193 Find similar reactions

A: 18 % Chromat. B: 6 % Chromat. C: 76 % Chromat.

With sodium peroxodisulphate in water

T=85 - 90°C; 8 h; other reaction time; Product distribution;

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

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1984 , vol. 33, p. 1887 - 1891 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1984 , # 9 p. 2068 - 2073 Title/Abstract Full Text View citing articles Show Details

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301

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Rx-ID: 44196185 Find similar reactions

With 5 platinum on carbon; nitrogen(II) oxide

T=80°C; P=11400.8 Torr; 2 h; Inert atmosphere; TemperatureReagent/catalyst;

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ;

Location in patent: Paragraph 0138; 0139-0142 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

5-1:Deamination of homoserine lactone hydrochloride using methanol as a solvent

The reactor was charged with 1 g of HSL · HCl, 40 g of methanol and 0.05 g of Pt (5) / Ac, followed by NO / N2 (15 atm, 1: 1 (v / v) As above, additional H2 (6.5 atm) was added and the desmethylation reaction of HSL.HCl was performed. The product was partially recovered and the components were analyzed. The results are shown in Table 8 below. A

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302

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A: 17% B: 28%

With 1-methoxy-4-nitropyridinium tetrafluoroborate in acetonitrile

5 h; Irradiationfurther reagent: nitrobenzene;

Negele, Stephan; Wieser, Katja; Severin, Theodor

Journal of Organic Chemistry, 1998 , vol. 63, # 4 p. 1138 - 1143 Title/Abstract Full Text View citing articles Show Details

A: 17% B: 28%

With 1-methoxy-4-nitropyridinium tetrafluoroborate in acetonitrile

5 h; Irradiationnitrobenzene;

Negele, Stephan; Wieser, Katja; Severin, Theodor

Journal of Organic Chemistry, 1998 , vol. 63, # 4 p. 1138 - 1143 Title/Abstract Full Text View citing articles Show Details

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303

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With 1-methoxy-4-nitropyridinium tetrafluoroborate in acetone

5 h; Irradiationfurther reagent: nitrobenzene; Yield given;

Negele, Stephan; Wieser, Katja; Severin, Theodor

Journal of Organic Chemistry, 1998 , vol. 63, # 4 p. 1138 - 1143 Title/Abstract Full Text View citing articles Show Details

304

Synthesize Find similar Rx-ID: 39393080 Find similar reactions

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305

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Rx-ID: 1562454 Find similar reactions

A: 25% B: 7% C: 55%

With carbon; zinc in tetrahydrofuran

T=20°C;

Boldrini, Gian Paolo; Savoia, Diego; Tagliavini, Emilio; Trombini, Claudio; Umani-Ronchi, Achille

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4108 - 4111 Title/Abstract Full Text View citing articles Show Details

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306

Synthesize Find similar Rx-ID: 3317951 Find similar reactions

B: 15%

Heating;

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Vinogradov, Mikhail M.; Kozlov, Yuriy N.; Bilyachenko, Alexey N.; Nesterov, Dmytro S.; Shul'pina, Lidia S.; Zubavichus, Yan V.; Pombeiro, Armando J. L.; Levitsky, Mikhail M.; Yalymov, Alexey I.; Shul'pin, Georgiy B.

New Journal of Chemistry, 2015 , vol. 39, # 1 p. 187 - 199 Title/Abstract Full Text View citing articles Show Details

With [(PhSiO1.5)12(CuO)4(NaO0.5)4]; nitric acid; (18)O2 in acetonitrile

T=60°C; P=750.075 Torr; Kinetics; Reagent/catalyst;

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Dardoize; Goasdoue; Goadoue; Laborit; Topall

Tetrahedron, 1989 , vol. 45, # 24 p. 7783 - 7794 Title/Abstract Full Text View citing articles Show Details

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307

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Rx-ID: 29349146 Find similar reactions

A: 8% B: 5.7% C: 86.3%

With hydrogen in 1,4-dioxane; methanol

T=200°C; P=60006 Torr; 20 h; Inert atmosphereAutoclave; Reagent/catalyst; Show Experimental Procedure

Hong, Ung Gi; Kim, Jeong Kwon; Lee, Joongwon; Lee, Jong Kwon; Yi, Jongheop; Song, In Kyu

Journal of Nanoscience and Nanotechnology, 2014 , vol. 14, # 11 p. 8867 - 8872 Title/Abstract Full Text View citing articles Show Details

A: 76 %Chromat. B: 6 %Chromat. C: 14 %Chromat.

With Ru(acac)3; hydrogen; zinc; 1,1,1-tris (diphenylphosphinomethyl)ethane

T=20 - 120°C; P=60006 Torr; Autoclave;

Rosi, Luca; Frediani, Marco; Frediani, Piero

Journal of Organometallic Chemistry, 2010 , vol. 695, # 9 p. 1314 - 1322 Title/Abstract Full Text View citing articles Show Details

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308

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Rx-ID: 29349147 Find similar reactions

A: 14 %Chromat. B: 56 %Chromat. C: 28 %Chromat.

With Ru(acac)3; hydrogen; zinc; 1,1,1-tris (diphenylphosphinomethyl)ethane

T=20 - 120°C; P=60006 Torr; Autoclave;

Rosi, Luca; Frediani, Marco; Frediani, Piero

Journal of Organometallic Chemistry, 2010 , vol. 695, # 9 p. 1314 - 1322 Title/Abstract Full Text View citing articles Show Details

309

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Rx-ID: 29349148 Find similar reactions

A: 14 %Chromat. B: 38 %Chromat. C: 48 %Chromat.

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With Ru(acac)3; hydrogen; zinc; 1,1,1-tris (diphenylphosphinomethyl)ethane

T=20 - 120°C; P=60006 Torr; Autoclave;

Rosi, Luca; Frediani, Marco; Frediani, Piero

Journal of Organometallic Chemistry, 2010 , vol. 695, # 9 p. 1314 - 1322 Title/Abstract Full Text View citing articles Show Details

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310

Synthesize Find similar Rx-ID: 34491463 Find similar reactions

With gold nanoparticles supported on titanium oxide; oxygen; sodium methylate in methanol

T=100°C; P=7500.75 Torr; Autoclave; Solvent;

D'Agostino, Carmine; Brett, Gemma L.; Miedziak, Peter J.; Knight, David W.; Hutchings, Graham J.; Gladden, Lynn F.; Mantle, Mick D.

Chemistry - A European Journal, 2012 , vol. 18, # 45 p. 14426 - 14433 Title/Abstract Full Text View citing articles Show Details

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311

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Rx-ID: 29627446 Find similar reactions

Lammens, Tijs M.; Franssen, Maurice C. R.; Scott, Elinor L.; Sanders, Johan P. M.

Green Chemistry, 2010 , vol. 12, # 8 p. 1430 - 1436 Title/Abstract Full Text View citing articles Show Details

With NH4Br

T=250°C; P=3750.38 Torr; 5.33333 h; Inert atmosphereAutoclave;

312

Synthesize Find similar Rx-ID: 35974147 Find similar reactions

A: 2% B: 4% C: 5% E: 17% F: 18% G: 2% H: 30% I: 3%

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With oxygen in acetone

T=20°C; 6 h; Irradiation;

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Novikov; Shestak

Russian Chemical Bulletin, 2012 , vol. 61, # 6 p. 1099 - 1110 Izv. Akad. Nauk, Ser. Khim., 2012 , # 6 p. 1092 - 1102,11 Title/Abstract Full Text View citing articles Show Details

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313

Synthesize Find similar Rx-ID: 35974150 Find similar reactions

A: 1% B: 3% C: 3% D: 13% E: 36% F: 1% G: 22% H: 2%

With oxygen in acetone

T=20°C; 4 h; Irradiation;

Novikov; Shestak

Russian Chemical Bulletin, 2012 , vol. 61, # 6 p. 1099 - 1110 Izv. Akad. Nauk, Ser. Khim., 2012 , # 6 p. 1092 - 1102,11 Title/Abstract Full Text View citing articles Show Details

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314

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Rx-ID: 40830791 Find similar reactions

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Shokri, Alireza; Que, Lawrence

Journal of the American Chemical Society, 2015 , vol. 137, # 24 p. 7686 - 7691 Title/Abstract Full Text View citing articles Show Details

With [(1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane)FeIII(O2)]2+ in tetrahydrofuran

T=-10°C; Inert atmosphereGlovebox; Reagent/catalyst; A

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315

Synthesize Find similar Rx-ID: 35974143 Find similar reactions

A: 3% B: 31% C: 2% D: 4% E: 27% F: 4% G: 28%

With 2,6-di-tert-butyl-4-methyl-phenol; oxygen in acetone

7.5 h; Irradiation;

Novikov; Shestak

Russian Chemical Bulletin, 2012 , vol. 61, # 6 p. 1099 - 1110 Izv. Akad. Nauk, Ser. Khim., 2012 , # 6 p. 1092 - 1102,11 Title/Abstract Full Text View citing articles Show Details

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316

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A: 1% B: 9% C: 18% D: 45% E: 17%

With 2,6-di-tert-butyl-4-methyl-phenol; oxygen in acetone

3.5 h; Irradiation;

Novikov; Shestak

Russian Chemical Bulletin, 2012 , vol. 61, # 6 p. 1099 - 1110 Izv. Akad. Nauk, Ser. Khim., 2012 , # 6 p. 1092 - 1102,11 Title/Abstract Full Text View citing articles Show Details

317

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Rx-ID: 27931213 Find similar reactions

A: 30% B: 37%

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With manganese(IV) oxide; lithium hydroxide; 4 Angstroem MS in tetrahydrofuran

8 h; Heating;

Phillips, David J.; Graham, Andrew E.

Synlett, 2008 , # 5 p. 649 - 652 Title/Abstract Full Text View citing articles Show Details

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318

Synthesize Find similar Rx-ID: 3980456 Find similar reactions

A: 57% B: 15%

With hydrogenchloride in water

0.166667 h; Ambient temperaturestudy of the acid catalyzed hydrolysis reaction of various unsaturated spiroorthoesters, mechanism is discussed; Product distribution;

Tagoshi, Hirotaka; Endo, Takeshi

Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 3 p. 945 - 947 Title/Abstract Full Text Show Details

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319

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A: 2% B: 4% C: 40% D: 2% E: 40%

With dihydrogen peroxide in tert-butyl alcohol

T=20°C; 120 h;

Novikov; Shestak

Russian Chemical Bulletin, 2013 , vol. 62, # 10 p. 2171 - 2190 Izv. Akad. Nauk, Ser. Khim., 2013 , vol. 62, # 10 p. 2171 - 2190,20 Title/Abstract Full Text View citing articles Show Details

F: 3% A

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320

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A: 1% B: 62% C: 1% D: 3% E: 18% F: 4% G: 6% H: 2%

With dihydrogen peroxide in acetic acid

3 h; Reflux;

Novikov; Shestak

Russian Chemical Bulletin, 2013 , vol. 62, # 10 p. 2171 - 2190 Izv. Akad. Nauk, Ser. Khim., 2013 , vol. 62, # 10 p. 2171 - 2190,20 Title/Abstract Full Text View citing articles Show Details

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321

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A: 30% B: 11% C: 12% D: 7% E: 61%

Maillard, Bernard; Manigand, Claude; Pavlovna Tarassova, Natalia; Villenave, Jean-Jacques; Filliatre, Claude

Bulletin de la Societe Chimique de France, 1981 , vol. 2, # 7-8 p. 255 - 260 Title/Abstract Full Text Show Details

in various solvent(s) T=120°C; 14 h; MechanismProduct distribution;

322

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A: 1% C: 0.4% F: 98% G: 0.5%

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With hydrogen; copper catalyst, T 4489, Sud-Chemie AG, Munich T=150 - 280°C; P=187519 Torr; Neat liquid(s) and gas(es)/vapour(s);

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BASF Aktiengesellschaft

Patent: US6350924 B1, 2002 ; Location in patent: Example 1 ; Title/Abstract Full Text Show Details

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323

Synthesize Find similar Rx-ID: 2980748 Find similar reactions

With sodium hydride

1) room temperature, overnight, 2) irradiation, -78 deg C, 5 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

Stapersma, J.; Rood, I. D. C.; Klumpp, G. W.

Tetrahedron, 1982 , vol. 38, # 1 p. 191 - 199 Title/Abstract Full Text View citing articles Show Details

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324

Synthesize Find similar Rx-ID: 1830108 Find similar reactions

With hydrogen; iron RFC

T=280 - 300°C; P=15001.2 - 22501.8 Torr; Product distributionMechanism;

325

Kliger, G. A.; Lesik, O. A.; Marchevskaya, E. V.; Mikaya, A. I.; Zaikin, V. G.; et al.

Chemistry of Heterocyclic Compounds (New York, NY, United States), 1987 , vol. 23, # 2 p. 161 - 164 Khimiya Geterotsiklicheskikh Soedinenii, 1987 , vol. 23, # 2 p. 195 - 198 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2991845 Find similar reactions

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Stapersma, J.; Rood, I. D. C.; Klumpp, G. W.

Tetrahedron, 1982 , vol. 38, # 20 p. 3051 - 3058 Title/Abstract Full Text View citing articles Show Details

1) NaH, THF, r.t., 2h, exclusion of light; 2) irradiation, THF, -78 deg C; Multistep reaction;

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326

Synthesize Find similar Rx-ID: 23659043 Find similar reactions

A: 0.86% B: 4.34% C: 0.28% D: 1.24% E: 0% F: 85.51% G: 0% H: 0.04% I: 0% J: 0%

With hydrogen; 0.5percent Pd/0.2percent Re on Rutile TiO2

T=110°C; 170 - 1009 h; Product distribution / selectivity; Hide Experimental Procedure

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 13 ; Title/Abstract Full Text Show Details

Tables 2a and 2b show the results of hydrogenation of maleic acid to succinic acid over several sample time periods using catalysts prepared as described in Catalyst Example 1(a) and Catalyst Example 2. A

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327

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Rx-ID: 2329011 Find similar reactions

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Anklam, Elke; Margaretha, Paul

Helvetica Chimica Acta, 1983 , vol. 66, # 5 p. 1466 - 1474 Title/Abstract Full Text Show Details

in acetonitrile

3 h; Irradiation; Yield given. Further byproducts given;

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328

Synthesize Find similar Rx-ID: 2329026 Find similar reactions

Anklam, Elke; Margaretha, Paul

Helvetica Chimica Acta, 1983 , vol. 66, # 5 p. 1466 - 1474 Title/Abstract Full Text Show Details

in acetonitrile

3 h; Irradiation; Yield given. Further byproducts given;

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329

Synthesize Find similar Rx-ID: 29149642 Find similar reactions

A: 41 %Chromat. B: 15 %Chromat.

With cyclohexa-1,4-diene in benzene-d6

T=135°C; Bergman cyclization; 72 h; Inert atmosphere;

Baroudi, Abdulkader; Mauldin, Justin; Alabugin, Igor V.

Journal of the American Chemical Society, 2010 , vol. 132, # 3 p. 967 - 979 Title/Abstract Full Text View citing articles Show Details

330

Synthesize Find similar Rx-ID: 3082421 Find similar reactions

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A: 28% B: 2%

With potassium carbonate in acetonitrile

12 h; Heating;

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 Full Text Show Details

A: 28% B: 2%

With potassium carbonate in acetonitrile

12 h; Heating;

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 Full Text Show Details

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331

Synthesize Find similar Rx-ID: 1642002 Find similar reactions

A: 75% B: 5% C: 8% D: 12%

With sodium hydroxide in ethanol; water

T=200°C; 2 h;

Lipkin, M.A.; Markevich, V.S.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, p. 1607 - 1608 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 8 p. 1782 - 1783 Title/Abstract Full Text Show Details

A: 75% B: 3% C: 8% D: 12%

With sodium hydroxide in ethanol; water

T=200°C; 2 h;

Lipkin, M.A.; Markevich, V.S.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, p. 1607 - 1608 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 8 p. 1782 - 1783 Title/Abstract Full Text Show Details

A: 15% B: 16% C: 4% D: 62%

With sodium hydroxide in ethanol; water

T=200°C; 2 h; other reagent/educt ratio,; Product distribution;

Lipkin, M.A.; Markevich, V.S.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, p. 1607 - 1608 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 8 p. 1782 - 1783 Title/Abstract Full Text Show Details

Hide Details

A: 15% B: 16% C: 4% D: 62%

With sodium hydroxide in ethanol; water

T=200°C; 2 h;

Lipkin, M.A.; Markevich, V.S.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, p. 1607 - 1608 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 8 p. 1782 - 1783 Title/Abstract Full Text Show Details

A: 15% B: 16% C: 4% D: 62%

With sodium hydroxide in ethanol; water

T=200°C; 2 h;

Lipkin, M.A.; Markevich, V.S.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, p. 1607 - 1608 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 8 p. 1782 - 1783 Title/Abstract Full Text Show Details

332

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Rx-ID: 28331334 Find similar reactions

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Budroni, Gerolamo; Corma, Avelino

Journal of Catalysis, 2008 , vol. 257, # 2 p. 403 - 408 Title/Abstract Full Text View citing articles Show Details

With Au-TiO2 nanoparticles; hydrogen in 1,4-dioxane

T=250°C; P=110 Torr;

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333

Synthesize Find similar Rx-ID: 23058585 Find similar reactions

A: 5.3% C: 10.4% H: 79.1%

With hydrogen

T=190°C; P=46504.7 Torr; Gas phase;

BASF Aktiengesellschaft

Patent: US6350924 B1, 2002 ; Location in patent: Page column 7 ; Title/Abstract Full Text Show Details

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334

Synthesize Find similar Rx-ID: 38749750 Find similar reactions

With hydrogenchloride in chloroform-d1

T=37°C; 24 h;

Zhang, Li-Jing; Deng, Xin-Xing; Du, Fu-Sheng; Li, Zi-Chen

Macromolecules, 2013 , vol. 46, # 24 p. 9554 - 9562 Title/Abstract Full Text View citing articles Show Details

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335

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Rx-ID: 1848120 Find similar reactions

Wiberg, Kenneth B.; Waldron, Boy F.

Journal of the American Chemical Society, 1991 , vol. 113, # 20 p. 7705 - 7709 Title/Abstract Full Text View citing articles Show Details

in dichloromethane-d2

T=25°C; Equilibrium constantRate constant;

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336

Synthesize Find similar Rx-ID: 34242396 Find similar reactions

C: 57%

With O-(diphenylphosphinyl)hydroxylamine in toluene

T=20 - 85°C; chemoselective reaction;

Laulhe, Sebastien; Gori, Sadakatali S.; Nantz, Michael H.

Journal of Organic Chemistry, 2012 , vol. 77, # 20 p. 9334 - 9337,4 Title/Abstract Full Text Show Details

Laulhé, Sébastien; Gori, Sadakatali S.; Nantz, Michael H.

Journal of Organic Chemistry, 2012 , vol. 77, # 20 p. 9334 - 9337 Title/Abstract Full Text View citing articles Show Details

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337

Synthesize Find similar Rx-ID: 1496871 Find similar reactions

C: 1.25 g

With dipyridinium dichromate; molecular sieve in dichloromethane

20 h; Ambient temperature; Yields of byproduct given;

Papaioannou, Dionissios; Francis, George W.; Aksnes, Dagfinn W.; Brekke, Trond; Maartmann-Moe, Knut

Acta Chemica Scandinavica, 1990 , vol. 44, # 1 p. 90 - 95 Title/Abstract Full Text Show Details

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338

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Rx-ID: 6683083 Find similar reactions

Oldham

Journal of the Chemical Society, 1950 , p. 100,105 Full Text Show Details

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339

Synthesize Find similar Rx-ID: 1626414 Find similar reactions

With electrochemical reduction by-products; Product distribution;

Shirobokova, O. I.; Adamov, A. A.; Freidlin, G. N.; Antonenko, N. S.; Grudtsyn, Yu. D.

J. Appl. Chem. USSR (Engl. Transl.), 1987 , vol. 60, # 11 p. 2619 - 2620,2428 - 2429 Title/Abstract Full Text Show Details

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340

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Zhidkova, N. V.; Kobryanskii, V. M.; Turovskaya, L. M.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1986 , vol. 35, p. 1462 - 1465 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986 , # 7 p. 1612 - 1615 Title/Abstract Full Text View citing articles Show Details

With boron trifluoride diethyl etherate in dichloromethane

T=20°C; 63.5667 h; other reaction time; also with other HX (X =Cl, OH); also in the absence of BF3*Et2O; Product distribution;

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341

Synthesize Find similar Rx-ID: 2476968 Find similar reactions

B: 3% D: 39%

With ozone in polyethylene

T=-75°C; 10 h;

Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes

Chemische Berichte, 1991 , vol. 124, # 2 p. 391 - 396 Title/Abstract Full Text Show Details

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342

Synthesize Find similar Rx-ID: 29820754 Find similar reactions

Ding, Guoqiang; Zhu, Yulei; Zheng, Hongyan; Zhang, Wei; Li, Yongwang

Catalysis Communications, 2010 , vol. 11, # 14 p. 1120 - 1124 Title/Abstract Full Text View citing articles Show Details

With ZnCuO2; hydrogen

T=170°C; P=30003 Torr; 0.000361111 h;

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343

Synthesize Find similar Rx-ID: 40853119

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With calcium chloride

T=150°C; 8 h;

Yamasaki, Ryu; Sudo, Atsushi; Endo, Takeshi

Journal of Polymer Science, Part A: Polymer Chemistry, 2015 , vol. 53, # 21 p. 2462 - 2468 Title/Abstract Full Text View citing articles Show Details

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344

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Rx-ID: 3851191 Find similar reactions

A: 8.9 % Chromat. B: 2.4 % Chromat. C: 45% D: 11%

Hoberg, Heinz; Riegel, Hans Josef

Journal of Organometallic Chemistry, 1983 , vol. 241, # 2 p. 245 - 250 Title/Abstract Full Text View citing articles Show Details

in tetrahydrofuran; diethyl ether

P=750.06 Torr; Ambient temperature;

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345

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Rx-ID: 11194093 Find similar reactions

A: 5% D: 91%

With manganese(IV) oxide in dichloromethane

T=20°C; Wittig olefination; 48 h;

Phillips, David J.; Pillinger, Kathryn S.; Li, Wei; Taylor, Angela E.; Graham, Andrew E.

Tetrahedron, 2007 , vol. 63, # 42 p. 10528 - 10533 Title/Abstract Full Text View citing articles Show Details

346

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A: 76% B: 24%

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With sodium iodide in dichloromethane; acetonitrile

Beaulieu, Normand; Deslongchamps, Pierre

Canadian Journal of Chemistry, 1980 , vol. 58, p. 164 - 167 Title/Abstract Full Text Show Details

With sodium iodide in dichloromethane; acetonitrile

Beaulieu, Normand; Deslongchamps, Pierre

Canadian Journal of Chemistry, 1980 , vol. 58, p. 164 - 167 Title/Abstract Full Text Show Details

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347

Synthesize Find similar Rx-ID: 29149638 Find similar reactions

A: 31 %Spectr. B: 11 %Spectr. C: 10 %Spectr.

With cyclohexa-1,4-diene in benzene-d6

T=135°C; Bergman cyclization; 48 h; Inert atmosphere;

Baroudi, Abdulkader; Mauldin, Justin; Alabugin, Igor V.

Journal of the American Chemical Society, 2010 , vol. 132, # 3 p. 967 - 979 Title/Abstract Full Text View citing articles Show Details

A: 6 %Spectr. B: 73 %Spectr. C: 6 %Spectr.

With cyclohexa-1,4-diene in benzene-d6

T=135°C; Bergman cyclization; 48 h; Inert atmosphere;

Baroudi, Abdulkader; Mauldin, Justin; Alabugin, Igor V.

Journal of the American Chemical Society, 2010 , vol. 132, # 3 p. 967 - 979 Title/Abstract Full Text View citing articles Show Details

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348

Synthesize Find similar Rx-ID: 1705800 Find similar reactions

T=275°C; 1.5 h; Yield given. Yields of byproduct given;

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Lipkin, M.A.; Markevich, V.S.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, p. 1609 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 8 p. 1785 Title/Abstract Full Text Show Details

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349

Synthesize Find similar Rx-ID: 38749749 Find similar reactions

With hydrogenchloride in chloroform-d1

T=37°C; 5 h;

Zhang, Li-Jing; Deng, Xin-Xing; Du, Fu-Sheng; Li, Zi-Chen

Macromolecules, 2013 , vol. 46, # 24 p. 9554 - 9562 Title/Abstract Full Text View citing articles Show Details

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350

Synthesize Find similar Rx-ID: 38749751 Find similar reactions

Zhang, Li-Jing; Deng, Xin-Xing; Du, Fu-Sheng; Li, Zi-Chen

Macromolecules, 2013 , vol. 46, # 24 p. 9554 - 9562 Title/Abstract Full Text View citing articles Show Details

in hexadeuterioacetone; water-d2

T=37°C; pH=7.4; 7 h;

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351

Synthesize Find similar Rx-ID: 2326747 Find similar reactions

A: 32% B: 68%

With sodium iodide in dichloromethane; acetonitrile

Beaulieu, Normand; Deslongchamps, Pierre

Canadian Journal of Chemistry, 1980 , vol. 58, p. 164 - 167

Title/Abstract Full Text Show Details

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352

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Rx-ID: 3914324 Find similar reactions

With acetic acid; methyl iodide; Ru(acac)3

T=200°C; P=112509 Torr; 12 h; Further byproducts given;

Braca, G.; Sbrana, G.; Galletti, A. M. Raspolli; Berti, S.

Journal of Organometallic Chemistry, 1988 , vol. 342, p. 245 - 258 Title/Abstract Full Text View citing articles Show Details

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353

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Rx-ID: 3535684 Find similar reactions

A: 6.7 g B: 4.9 g

in methanol

T=10°C; 0.5 h;

Voronkov, M. G.; Vvedenskii, V. Yu.

J. Gen. Chem. USSR (Engl. Transl.), 1984 , vol. 54, # 7 p. 1674 - 1675,1491 - 1492 Title/Abstract Full Text Show Details

A: 6.7 g B: 4.9 g

in methanol

T=10°C; 0.5 h;

Voronkov, M. G.; Vvedenskii, V. Yu.

J. Gen. Chem. USSR (Engl. Transl.), 1984 , vol. 54, # 7 p. 1674 - 1675,1491 - 1492 Title/Abstract Full Text Show Details

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354

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Rx-ID: 35974141 Find similar reactions

A: 1% B: 2% C: 7% E: 7% F: 0.014 g G: 2% H: 13% I: 38% J: 2% K: 5% L: 11% M: 2%

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With oxygen; calcium chloride in acetone

T=57°C; 30 h;

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Novikov; Shestak

Russian Chemical Bulletin, 2012 , vol. 61, # 6 p. 1099 - 1110 Izv. Akad. Nauk, Ser. Khim., 2012 , # 6 p. 1092 - 1102,11 Title/Abstract Full Text View citing articles Show Details

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355

Synthesize Find similar Rx-ID: 35974144 Find similar reactions

A: 2% B: 12% C: 30% D: 12% E: 32% F: 3% G: 2% H: 3%

With oxygen in tetrachloromethane

T=20°C; 4.5 h; Irradiation;

Novikov; Shestak

Russian Chemical Bulletin, 2012 , vol. 61, # 6 p. 1099 - 1110 Izv. Akad. Nauk, Ser. Khim., 2012 , # 6 p. 1092 - 1102,11 Title/Abstract Full Text View citing articles Show Details

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356

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Rx-ID: 11194090 Find similar reactions

C: 5% D: 66%

With manganese(IV) oxide in dichloromethane

T=20°C; Wittig olefination; 24 h;

Phillips, David J.; Pillinger, Kathryn S.; Li, Wei; Taylor, Angela E.; Graham, Andrew E.

Tetrahedron, 2007 , vol. 63, # 42 p. 10528 - 10533 Title/Abstract Full Text View citing articles Show Details

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357

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Rx-ID: 327586 Find similar reactions

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Child; Pyman

Journal of the Chemical Society, 1931 , p. 36,47 Full Text Show Details

in feuchtem Zustand;

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358

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Rx-ID: 10193711 Find similar reactions

With Grubb's 2nd generation catalyst in dichloromethane

T=20°C; 6 h;

Finnegan, David; Seigal, Benjamin A.; Snapper, Marc L.

Organic Letters, 2006 , vol. 8, # 12 p. 2603 - 2606 Title/Abstract Full Text View citing articles Show Details

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359

Synthesize Find similar Rx-ID: 26936886 Find similar reactions

standing on air;

Masters, Andrew P.; Sorensen, Ted S.

Canadian Journal of Chemistry, 1990 , vol. 68, # 3 p. 502 - 506 Title/Abstract Full Text Show Details

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360

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Rx-ID: 1866227 Find similar reactions

With aluminium(III) iodide; acetic acid; Ru(acac)3

T=200°C; P=105008 Torr; 8 h; Product distributionMechanism;

Braca, G.; Sbrana, G.; Galletti, A. M. Raspolli; Berti, S.

Journal of Organometallic Chemistry, 1988 , vol. 342, p. 245 - 258 Title/Abstract Full Text View citing articles Show Details

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361

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Rx-ID: 3914325 Find similar reactions

With acetic acid; methyl iodide; Ru(acac)3

T=200°C; P=112509 Torr; 12 h; various time; Product distributionMechanism;

Braca, G.; Sbrana, G.; Galletti, A. M. Raspolli; Berti, S.

Journal of Organometallic Chemistry, 1988 , vol. 342, p. 245 - 258 Title/Abstract Full Text View citing articles Show Details

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362

Synthesize Find similar Rx-ID: 38493397 Find similar reactions

B: 89%

in ethanol

T=78°C; 4 h; Hide Experimental Procedure

Glotova, Tatyana E.; Dvorko, Marina Yu.; Ushakov, Igor A.; Shabalin, Dmitrii A.; Schmidt, Elena Yu.; Trofimov, Boris A.

Mendeleev Communications, 2012 , vol. 22, # 6 p. 314 - 316 Title/Abstract Full Text View citing articles Show Details

Synthesis of 3-acyl-2,6-diphenylpyridines 6a-c.

General procedure: Compound 5a-c (0.5 mmol) was dissolved in EtOH (10 ml) and stirred at 78 °C for 4 h. The solvent was half-evaporated, the concentrate was kept at ~0 °C forone day, the crystals precipitated were filtered off and dried in vacuo. A

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363

Synthesize Find similar Rx-ID: 26838383 Find similar reactions

decompn. at 240°C;

Yamaji, Y.; Ninomiya, K.; Matsuda, H.; Matsuda, S.

Kogyo Kagaku Zasshi, 1971 , vol. 74, p. 1181 - 1184 Full Text Show Details

decompn. at 240°C;

Gmelin Handbook: Sn: Org.Comp.12, 1.4.1.1.1.5.4.4, page 147 - 166 Full Text Show Details

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364

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B: 83%

Glotova, Tatyana E.; Dvorko, Marina Yu.; Ushakov, Igor A.; Shabalin, Dmitrii A.; Schmidt, Elena Yu.; Trofimov, Boris A.

Mendeleev Communications, 2012 , vol. 22, # 6 p. 314 - 316 Title/Abstract Full Text View citing articles Show Details

in ethanol

T=78°C; 4 h; Hide Experimental Procedure

Synthesis of 3-acyl-2,6-diphenylpyridines 6a-c.

365

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Rx-ID: 38493398 Find similar reactions

B: 82%

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Glotova, Tatyana E.; Dvorko, Marina Yu.; Ushakov, Igor A.; Shabalin, Dmitrii A.; Schmidt, Elena Yu.; Trofimov, Boris A.

Mendeleev Communications, 2012 , vol. 22, # 6 p. 314 - 316 Title/Abstract Full Text View citing articles Show Details

in ethanol

T=78°C; 4 h; Hide Experimental Procedure

Synthesis of 3-acyl-2,6-diphenylpyridines 6a-c.

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366

Rx-ID: 24904566 Find similar reactions

Allergan, Inc.

Patent: US5134128 A1, 1992 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

30:4-(1-acetoxytridecyl)-5-hydroxy-2-tetrahydrofuranone

EXAMPLE 30 4-(1-acetoxytridecyl)-5-hydroxy-2-tetrahydrofuranone A solution of 4-(1-acetoxytridecyl)-5-hydroxy-2(5H)-furanone (0.11 g, 0.32 mmol) and 5percent rhodium on alumina (24 mg) in 6 ml of methanol was stirred rapidly under a hydrogen atmosphere for two hours. The mixture was concentrated, taken up in ethyl acetate, filtered through celite, and concentrated to give the tetrahydrofuranone as a colorless glass. 1 H NMR (mixture of diasteriomers) (CDCl ): 5.75 (brs, 1H, sharpens to 2S, 5.81 and 5.69 on D O exchange); 5.15 (brm, 1H, sharpens to 2 m, 5.20 and 5.19 and ls, 4.83 on D O exchange), 2.4 (m, 3H); 2.08 and 2.06 (2 s, 3H); 1.3 (m); 0.88 (t, J=6.6 Hz, 3H). 3 2 2 13

C NMR (mixture of diasteriomers) (CDCl3): 176.0, 171.1, 101.1, 73.1 and 72.3, 60.5, 46.2, 32.4, 31.8, 30.8, 29.6, 29.4, 29.3, 29.25, 29.20, 29.0, 28.6, 25.2, 22.6, 20.8, 14.0.

m/z Calculated for C22 H43 O5 Si (M=TMS): 415.2880, obtained (CI+): 415.2897.

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367

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With H2 in benzene

High Pressure; hydrogenation at higher temp. and higher pressure; presence of phosphines, phosphites, arsines, stibines inhibits formation of butyric acid;

Sato, S.; Morishima, A.; Wakamatsu, H.

Nippon Kagaku Zasshi, 1970 , vol. 91, p. 557 - 561 C.A., 1970 , vol. 73, p. 120030 Full Text Show Details

Gmelin Handbook: Co: Org.Verb.2, 2.1.6, page 79 - 81 Full Text Show Details