methyl 2-oxo-2-phenylacetate
Benzoylformic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide | 100% |
With water; sodium hydroxide In dichloromethane | 100% |
With water; sodium hydroxide at 20℃; for 2h; | 99.2% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; | 100% |
With trifluoroacetic acid at 0℃; for 1h; | 57% |
With trifluoroacetic acid at 0℃; for 5h; |
Conditions | Yield |
---|---|
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 - 912.061 Torr; for 48h; chemoselective reaction; | A 91% B 99% |
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; ruthenium trichloride; potassium peroxymonosulfate / acetonitrile; water; ethyl acetate / 0.3 h 2: iron(II) perchlorate hexahydrate; tetramethylammonium hydroxide pentahydrate / acetonitrile; water / 12 h / Inert atmosphere View Scheme |
MANDELIC ACID
Benzoylformic acid
Conditions | Yield |
---|---|
With sodium bromate In acetonitrile for 52h; Heating; | 98% |
With oxalyl dichloride; methyl dodecyl sulfoxide; triethylamine In dichloromethane at -60 - 20℃; Swern oxidation; | 96% |
With oxalyl dichloride; methyl dodecyl sulfoxide; triethylamine In dichloromethane at -60 - 20℃; Swern oxidation; | 96% |
5-hydroxy-N,N',5-triphenylimidazolidine-2,4-dione
Benzoylformic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol at 20 - 50℃; for 1h; | 98% |
Conditions | Yield |
---|---|
With sulfuric acid at 100 - 120℃; for 5h; | 96.6% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; iron(III) chloride; thymidyl acetic acid In decane; acetonitrile at 80℃; for 6h; | 96% |
With Oxone; 2-Iodobenzoic acid In water; acetonitrile at 70℃; for 6h; | 94% |
With sodium tetrahydroborate; 1% Pd/C; water; potassium hydroxide In methanol at 20℃; for 15h; In air; | 91% |
With potassium permanganate; acetic acid; Tris(3,6-dioxaheptyl)amine In dichloromethane for 4h; Ambient temperature; | 71% |
aqua(2,2'-bipyridine)(2,2':6',2''-terpyridine)ruthenium(II)(2+) In phosphate buffer for 6h; pH=7.2; Electrolysis; | 47% |
Conditions | Yield |
---|---|
With tetramethoxytitanium; β-Propiolactone at 60℃; for 2h; Temperature; | 96% |
Multi-step reaction with 5 steps 1.1: hydrogen bromide; dihydrogen peroxide / water / 4.5 h / 25 - 90 °C 2.1: toluene-4-sulfonic acid; benzene / water / 36 h / 85 °C 3.1: tetrabutylammomium bromide; sodium ethanolate / water / 23 h / 105 °C 4.1: oxalic acid / dichloromethane; water / 5 h / 25 °C 5.1: tetrabutylammomium bromide; hydrogen bromide / water / 0.02 h 5.2: 5 h / 25 - 90 °C View Scheme |
Benzoylformic acid
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; | 94% |
Conditions | Yield |
---|---|
With phosphotungstic acid; ferric nitrate at 55 - 60℃; for 0.166667h; | 93% |
With D-lactate oxidase from Gluconobacter oxydans 621H; oxygen; catalase In aq. buffer at 30℃; pH=7.4; Reagent/catalyst; Enzymatic reaction; | |
With NAD at 30℃; for 48h; pH=9.5; Kinetics; Reagent/catalyst; Temperature; pH-value; Enzymatic reaction; |
MANDELIC ACID
Benzoylformic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hypobromide; sodium thiosulfate In dichloromethane; water | 91% |
Conditions | Yield |
---|---|
With hydrogen bromide; dihydrogen peroxide In water at 25 - 65℃; for 5h; Reagent/catalyst; Time; | 90.1% |
With hydrogen bromide; dihydrogen peroxide In water Temperature; Reflux; | 79.3% |
Stage #1: 1-phenyl-2-hydroxyethanone With tetrabutylammomium bromide; hydrogen bromide In water for 0.0166667h; Stage #2: With dihydrogen peroxide In water at 25 - 90℃; for 5h; | 83 %Chromat. |
With hydrogen bromide; dihydrogen peroxide In water at 90℃; for 7h; |
3,4-diphenyl-4-hydroxy-2-isoxazolin-5-one
A
benzonitrile
B
Benzoylformic acid
Conditions | Yield |
---|---|
With triethylamine In benzene for 3h; Heating; | A n/a B 89.3% |
With hydrogenchloride; sodium hydroxide; water Mechanism; |
epoxide of α,β-difluoro-β-chlorostyrene
Benzoylformic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate for 0.5h; | 89% |
Conditions | Yield |
---|---|
With pyridine; selenium(IV) oxide at 120℃; for 18h; Inert atmosphere; | 87% |
With pyridine; selenium(IV) oxide for 3h; Reflux; | 87% |
With pyridine; selenium(IV) oxide at 90℃; for 5h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With potassiuim nitrosodisulfonate In water for 60h; pH 10.0; | 82% |
With ω-transaminase |
2,2,2-Tris-benzotriazol-1-yl-1-phenyl-ethanone
Benzoylformic acid
Conditions | Yield |
---|---|
With sulfuric acid In tetrahydrofuran at 50℃; for 48h; | 81% |
3,5-diphenyl-4,4-dichloro-5-hydroxy-Δ2-isoxazoline
A
benzonitrile
B
Benzoylformic acid
Conditions | Yield |
---|---|
With potassium hydroxide In water for 2.5h; Heating; | A 75.4% B 80% |
Conditions | Yield |
---|---|
Stage #1: phenylglyoxal hydrate With silver perchlorate; sodium hydroxide In water at 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In water Inert atmosphere; | 78% |
bei der Einw. von gaerender Hefe; | |
Multi-step reaction with 2 steps 1: 26.5 percent Spectr. / Et3N, pyridine, O2, 3-Angstroem sieves / Cu(NO3)2py2 / methanol / 12 h / 25 °C / 1748 Torr 2: 68.6 percent Spectr. / Et3N, pyridine, O2, H2O / Cu(NO3)2py2 / methanol / 12 h / 25 °C / 1748 Torr View Scheme |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; magnesium In N,N-dimethyl-formamide at 20℃; Temperature; Solvent; | 75% |
Conditions | Yield |
---|---|
With hydrogenchloride; water; sodium nitrite at 80℃; for 4h; | 73.5% |
With acetic anhydride bei der Destillation u. Verseifen mit Salzsaeure; |
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; benzaldehyde With potassium cyanide In N,N-dimethyl-formamide at 12℃; for 1h; Schlenk technique; Stage #2: With titanium(IV)isopropoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 40℃; for 18h; Schlenk technique; | 72% |
diphenacyl sulfide
A
C16H10O4S
B
(3-phenylthiophene-2,5-diyl)bis(phenylmethanone)
C
Benzoylformic acid
Conditions | Yield |
---|---|
With selenium(IV) oxide In 1,4-dioxane for 2h; Reflux; | A n/a B 10% C 71% |
4-hydroxy-3-methyl-4-phenylisoxazoline-5-one
A
Benzoylformic acid
B
acetonitrile
Conditions | Yield |
---|---|
With 2,6-dichloro-benzonitrile In benzene for 0.5h; Heating; | A 70% B n/a |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; magnesium In N,N-dimethyl-formamide at 20℃; | 69% |
2-nitroacetophenone
A
Benzoylformic acid
B
benzoic acid
C
3,4-dibenzoyl-1,2,5-oxadiazole-N-oxide
Conditions | Yield |
---|---|
With nitric acid; sodium nitrite In nitromethane; water at 60℃; for 0.5h; | A 9.7% B 4.4% C 68.4% |
With nitric acid; sodium nitrite In nitromethane; water at 60℃; for 0.5h; Product distribution; Mechanism; variation of solvents, reactants; | A 9.7% B 4.4% C 68.4% |
iodobenzene
carbon monoxide
A
MANDELIC ACID
B
Benzoylformic acid
C
benzoic acid
Conditions | Yield |
---|---|
With methyl iodide; sodium tetrahydroborate In 1,4-dioxane; water at 20℃; for 20h; | A 3% B 68% C 5% |
With methyl iodide; sodium tetrahydroborate In 1,4-dioxane; water at 20℃; for 20h; | A 3% B 64% C 13% |
With calcium hydroxide; water; dichlorobis(dimethylphenylphosphine)palladium(II) In isopropyl alcohol at 100℃; for 12h; P(CO) = 150 atm at room temperature; further catalysts, solvents and hydroxide; | A 69.0 % Chromat. B 3.8 % Chromat. C 9.3 % Chromat. |
With calcium hydroxide; water; bis(benzonitrile)palladium(II) dichloride In isopropyl alcohol at 100℃; for 12h; P(CO) = 150 atm at room temperature; further catalysts, solvents and hydroxide; | A 46.0 % Chromat. B 8.7 % Chromat. C 25.5 % Chromat. |
With sodium sulfide; CoCl2 In 1,4-dioxane; water at 20℃; for 20h; Product distribution; other reag.; other solvent; | A 3 % Chromat. B 62 % Chromat. C 5 % Chromat. |
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane for 48h; | A 21% B 68% |
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetone for 48h; | A 65% B 11% |
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate; oxygen In acetonitrile at 60℃; | A 26% B 65% |
MANDELIC ACID
A
Benzoylformic acid
B
benzoic acid
Conditions | Yield |
---|---|
With oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile at 20℃; for 3h; | A 63% B 30% |
Benzoylformic acid
phenylglyoxylyl chloride
Conditions | Yield |
---|---|
With Dichloromethyl methyl ether at 50℃; for 0.5h; | 100% |
With Dichloromethyl methyl ether In dichloromethane at 15 - 20℃; for 1h; Inert atmosphere; | 100% |
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane | 95% |
Conditions | Yield |
---|---|
With sulfur In benzene at 80℃; for 0.166667h; | 100% |
With sulfur In benzene for 0.166667h; Heating; | 100% |
Conditions | Yield |
---|---|
With sulfur In benzene at 80℃; for 0.75h; | 100% |
With sulfur In benzene at 80℃; for 1h; |
Conditions | Yield |
---|---|
With sulfur In benzene at 80℃; for 0.75h; | 100% |
Conditions | Yield |
---|---|
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h; | 100% |
Stage #1: 1,4-pyrazine; Benzoylformic acid With ammonium peroxydisulfate; sulfuric acid; silver nitrate In dichloromethane; water at 50℃; for 2h; Stage #2: With water; sodium hydrogencarbonate In dichloromethane | 91% |
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; formic acid; dimethyl sulfoxide In dichloromethane; water at 40℃; Minisci Aromatic Substitution; | 74% |
With ammonium peroxydisulfate; silver nitrate; trifluoroacetic acid In dichloromethane; water at 60℃; for 3h; | 68% |
With dipotassium peroxodisulfate; silver orthophosphate In dichloromethane; water at 40℃; for 24h; | 26% |
methyl (4-pyridyl) ketone
Benzoylformic acid
1-(2-benzoylpyridin-4-yl)-ethanone
Conditions | Yield |
---|---|
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h; | 100% |
33% |
Conditions | Yield |
---|---|
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h; | 100% |
2,3-diethynylquinoxaline
Benzoylformic acid
phenyl(quinoxalin-2-yl)methanone
Conditions | Yield |
---|---|
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h; | 100% |
With dipotassium peroxodisulfate In water; acetonitrile at 20 - 37℃; for 15h; Irradiation; Green chemistry; regioselective reaction; | 80% |
With dipotassium peroxodisulfate; silver orthophosphate In dichloromethane; water at 40℃; for 24h; | 58% |
Conditions | Yield |
---|---|
100% |
1,2,3,4-tetrahydroisoquinoline
Benzoylformic acid
(3,4-dihydroisoquinoline-2(1H)-yl)(phenyl)methanethione
Conditions | Yield |
---|---|
With sulfur In benzene at 80℃; for 0.25h; | 100% |
With sulfur In benzene at 80℃; for 0.25h; |
Conditions | Yield |
---|---|
In dichloromethane at 40℃; for 3h; | 100% |
Conditions | Yield |
---|---|
Stage #1: oxalyl dichloride; Benzoylformic acid With copper diacetate; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Stage #2: diallylamine With triethylamine In dichloromethane | 100% |
(1S,2R)-(1-methyl-2-phenyl-2-hydroxy)ethyltrimethylammonium iodide
Benzoylformic acid
[(1R,2S)-N,N-dimethylephedrinium][phenylglyoxylate]
Conditions | Yield |
---|---|
With Dowex Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In chloroform for 0.5h; Inert atmosphere; Reflux; | 100% |
In chloroform for 0.5h; Inert atmosphere; Reflux; | 100% |
Conditions | Yield |
---|---|
In water; acetone | 100% |
Benzoylformic acid
Conditions | Yield |
---|---|
In isopropyl alcohol for 1h; Heating; | 99.2% |
Conditions | Yield |
---|---|
With chlorobenzene In methanol at 40℃; for 5h; Sealed tube; Green chemistry; chemoselective reaction; | 99% |
With phosphonic Acid; methanesulfonic acid; sodium iodide In water at 95℃; for 48h; Inert atmosphere; | 94.3% |
With hydrazine hydrate anschliessend Erhitzen mit KOH; | |
With phosphorus; hydrogen iodide at 160℃; |
(-)-8-phenylmenthol
Benzoylformic acid
Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Heating; | 99% |
With toluene-4-sulfonic acid In toluene at 130℃; for 2h; Dean-Stark; | 25% |
With hydrogen cation |
N,O-dimethylhydroxylamine*hydrochloride
Benzoylformic acid
N-methoxy-N-methyl-α-oxo-benzeneacetamide
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In acetonitrile at 20℃; for 1.5h; | 99% |
Stage #1: Benzoylformic acid With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0℃; for 0.25h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 20℃; for 1h; chemoselective reaction; | 75% |
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane for 0.75h; Heating; | 53% |
Benzoylformic acid
(1R,2R)-1,2-diphenyl-2-(4-trifluoromethylbenzyloxy)ethanol
(1R,2R)-1,2-diphenyl-2-(4-trifluoromethylbenzyloxy)ethyl phenylglyoxylate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; | 99% |
(1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethanol
Benzoylformic acid
oxophenylacetic acid (1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethyl ester
Conditions | Yield |
---|---|
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; | 99% |
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; |
(1R,2S)-1-(2-methoxyethoxy)-1,2-bis-(2-methoxyphenyl)-ethanol
Benzoylformic acid
oxophenylacetic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-bis(2-methoxyphenyl)ethyl ester
Conditions | Yield |
---|---|
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 12h; | 99% |
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 12h; |
diallylcarbonate
Benzoylformic acid
(E)-1-phenyl-2-buten-1-one
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); Tri(p-tolyl)phosphine In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate In water; acetonitrile at 70℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
With ammonium peroxydisulfate; copper(II) oxide In water; dimethyl sulfoxide at 80℃; for 12h; | 73% |
para-thiocresol
Benzoylformic acid
A
di(p-tolyl) disulfide
B
S-(4-methylphenyl) thiobenzoate
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate In water; acetonitrile at 70℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; | A 5.5% B 99% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate In water; acetonitrile at 70℃; for 24h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
phenylhydrazine
Benzoylformic acid
phenyl-((Z)-phenylhydrazono)-acetic acid
Conditions | Yield |
---|---|
With acetic acid In ethanol for 3h; Reflux; | 99% |
1. | ivn-mus LD50:180 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#04110 . |
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