Conditions | Yield |
---|---|
With boron trifluoride at 65℃; for 0.333333h; | 100% |
With sulfuric acid for 1h; Reflux; | 95% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 70℃; for 15h; | 95% |
diacetato(2,2'-bipyridine)palladium(II)
Dimethyl oxalate
Conditions | Yield |
---|---|
With 1,4-di(diphenylphosphino)-butane In dichloromethane-d2 at 25℃; Catalytic behavior; Reagent/catalyst; Time; | 100% |
methyl nitrite
carbon monoxide
A
Dimethyl oxalate
B
nitrogen(II) oxide
Conditions | Yield |
---|---|
With 0.5% Pd/C at 100℃; under 375.038 Torr; for 0.000555556h; Pressure; Reagent/catalyst; Temperature; Time; | A 98.9% B n/a |
diethyl phosphorylchloridite
methyl 2,2-dichloro-2-methoxyacetate
A
monomethyl oxalyl chloride
B
Dimethyl oxalate
C
chloroethane
D
phosphonic dichloride
E
methyl phosphonochloridate
F
ethyl phosphonochloridate
Conditions | Yield |
---|---|
With iron(III) chloride at 105 - 110℃; for 1.16667h; Product distribution; | A n/a B n/a C 95% D n/a E n/a F n/a |
diethyl phosphorylchloridite
methyl 2,2-dichloro-2-methoxyacetate
A
Dimethyl oxalate
B
phosphorodichloridous acid ethyl ester
C
chloroethane
D
phosphonic dichloride
E
ethyl phosphonochloridate
Conditions | Yield |
---|---|
With iron(III) chloride at 105 - 110℃; for 0.833333h; Product distribution; | A n/a B n/a C 95% D n/a E n/a F n/a |
Conditions | Yield |
---|---|
Stage #1: carbon dioxide With cesium bicarbonate; alumina at 325℃; under 18751.9 Torr; for 1h; Glovebox; Inert atmosphere; Stage #2: carbon monoxide at 325℃; under 15001.5 Torr; for 2h; Stage #3: methanol at 220℃; under 33753.4 Torr; for 1h; Reagent/catalyst; Pressure; Temperature; | 95% |
With methyl nitrite; nitrogen(II) oxide; palladium/alumina In water at 100℃; Industry scale; | |
Stage #1: carbon dioxide; carbon monoxide With alumina; caesium carbonate at 25 - 325℃; under 15001.5 - 18751.9 Torr; Glovebox; Stage #2: methanol at 150℃; under 26252.6 Torr; Glovebox; |
methanol
carbon dioxide
carbon monoxide
caesium carbonate
A
Dimethyl oxalate
B
cesium bicarbonate
C
cesium formate
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; carbon monoxide; caesium carbonate With silica gel; pyrographite at 325℃; under 15001.5 - 33753.4 Torr; Stage #2: methanol at 200℃; under 30003 Torr; for 2h; Reagent/catalyst; Temperature; Pressure; | A 95% B n/a C 0.8% |
Conditions | Yield |
---|---|
With pyridine In benzene for 30h; | 92% |
With pyridine In benzene at 20℃; for 30h; Inert atmosphere; Reflux; | 92% |
With pyridine In benzene for 3h; Inert atmosphere; Reflux; | 92% |
Conditions | Yield |
---|---|
Stage #1: carbon dioxide With hydrogen; caesium carbonate at 325℃; Glovebox; Stage #2: methanol at 150℃; | 89% |
A
Dimethyl oxalate
iron pentacarbonyl
Conditions | Yield |
---|---|
In dichloromethane-d2 byproducts: CO; introducing a soln. of Fe-complex in CD2Cl2 into NMR tube, maintaining temp. at 28°C under N2; monitoring by (13)C-NMR and gas chromatography; | A 15% B n/a C 85% |
With carbon monoxide In dichloromethane-d2 introducing a soln. of Fe-complex in CH2Cl2 into an autoclave thermostated at 34°C, stirring for 2.5 h under CO pressure; monitoring by (13)C-NMR and gas chromatography, cooling, removal of solvent under vacuum, redissolution in CD2Cl2, monitoring by (13)C-NMR; |
Conditions | Yield |
---|---|
for 2h; Solid phase reaction; esterification; | 67% |
fluorophosphoric acid diethyl ester
methyl 2,2-dichloro-2-methoxyacetate
A
Dimethyl oxalate
B
ethyl ethylphosphonofluoridate
C
ethylphosphonic chloride fluoride
D
methyl ethylphosphonofluoridate
E
ethyl phosphonofluoridate
Conditions | Yield |
---|---|
at 135 - 145℃; for 8h; Product distribution; | A 60% B n/a C n/a D n/a E n/a F n/a G n/a |
methanol
carbon dioxide
caesium carbonate
A
Dimethyl oxalate
B
cesium formate
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; caesium carbonate With hydrogen at 325℃; under 750.075 Torr; Stage #2: methanol at 150℃; under 26252.6 Torr; | A 58% B 10% |
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; caesium carbonate With hydrogen at 325℃; Stage #2: methanol at 150℃; | 54% |
methanol
5,5-Dichloro-3-cyclohexyl-oxazolidine-2,4-dione
A
Dimethyl oxalate
B
N-cyclohexyl-N-(methoxycarbonyl)oxamate
C
phenyl isocyanate
Conditions | Yield |
---|---|
With triethylamine In chloroform for 24h; Ambient temperature; | A n/a B 50% C n/a |
methanol
2,3-dimethoxy-1,3-butadiene
A
Dimethyl oxalate
B
methyl 2-methoxyacrylate
C
methoxymethyl hydroperoxide
D
2,3,3-Trimethoxy-4-hydroxy-1-butene
Conditions | Yield |
---|---|
With ozone at -30℃; | A 13 % Spectr. B 17% C 43% D 7% |
2,3-dimethoxy-1,3-butadiene
A
Dimethyl oxalate
B
methyl 2-methoxyacrylate
C
methoxymethyl hydroperoxide
D
2,3,3-Trimethoxy-4-hydroxy-1-butene
Conditions | Yield |
---|---|
With ozone In methanol at -30℃; | A n/a B 17% C 43% D 7% |
Conditions | Yield |
---|---|
sulfuric acid In methanol Heating; | 40% |
methyl 2-methoxyacrylate
A
Dimethyl oxalate
B
3-(Carboxymethyl)-3-methoxy-1,2-dioxolane
C
3-(Carboxymethyl)-3-methoxy-1,2,4-trioxolane
Conditions | Yield |
---|---|
With ozone at -75℃; for 3h; ozonolysis on polyethylene; | A n/a B 4% C 36% |
diazomethane
Methyl linoleate
A
Dimethyl oxalate
B
hexanedioic acid dimethyl ester
C
Dimethyl azelate
D
Dimethyl glutarate
E
dimethyl subarate
F
Dimethyl succinate
Conditions | Yield |
---|---|
With sodium hydroxide; 0 deg C; water; dihydrogen peroxide; ozone Product distribution; further conditions; | A n/a B 7.29% C 27.05% D 12.33% E 9.09% F 18.71% |
2,3-dimethoxy-1,3-butadiene
A
Dimethyl oxalate
B
methyl 2-methoxyacrylate
C
3-Methoxy-3-(1-methoxyethenyl)-1,2-dioxolane
D
3-Methoxy-3-(1-methoxyethenyl)-1,2,4-trioxolane
Conditions | Yield |
---|---|
With ozone In pentane at -30℃; | A n/a B n/a C 19% D 0.4% |
With ozone In pentane at -30℃; | A 19 % Spectr. B 34 % Spectr. C 19% D 0.4% |
2,3-dimethoxy-1,3-butadiene
A
Dimethyl oxalate
B
3-(Carboxymethyl)-3-methoxy-1,2-dioxolane
C
3-(Carboxymethyl)-3-methoxy-1,2,4-trioxolane
Conditions | Yield |
---|---|
With ozone In pentane at -30℃; | A n/a B 14% C 12% |
Conditions | Yield |
---|---|
In chloroform-d1 at 20℃; for 1h; | A n/a B 12% C 5.4% |
diazomethane
phenol; compound with oxalic acid
A
Dimethyl oxalate
B
methoxybenzene
methanol
bis(trichloromethyl) oxalate
A
Dimethyl oxalate
B
methyl chloroformate
methanol
oxalic acid
A
Dimethyl oxalate
B
oxalic acid monomethyl ester
Conditions | Yield |
---|---|
bei der Destillation; | |
With 20 molpercent molybdenum oxide nanoparticle supported on mesoporous silica at 75℃; for 8h; |
Dimethyl oxalate
potassium oxalate monomethyl ester
Conditions | Yield |
---|---|
With potassium acetate In methanol; water at 80℃; for 3h; | 100% |
With potassium acetate In methanol; water at 80℃; for 3h; | 91% |
With potassium acetate In methanol; water at 60℃; for 1h; | 80% |
With potassium acetate In methanol; water at 90℃; for 2h; Reflux; |
Dimethyl oxalate
3,5-dibromo-4-methoxy-phenyl acetic acid methyl ester
Conditions | Yield |
---|---|
With sodium methylate In methanol for 5h; Condensation; Heating; | 100% |
Dimethyl oxalate
4'-benzyloxy-acetophenone
sodium 3-(4-benzyloxyphenyl)-1-methoxycarbonyl-3-oxopropen-1-olate
Conditions | Yield |
---|---|
With sodium hydride In toluene at 60℃; for 3h; | 100% |
Dimethyl oxalate
1‐(6‐methoxypyridin‐3‐yl)ethan‐1‐one
4-(6-methoxy-3-pyridyl)-2,4-dioxobutanoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: Dimethyl oxalate; 1‐(6‐methoxypyridin‐3‐yl)ethan‐1‐one With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide pH=4; Product distribution / selectivity; | 100% |
Stage #1: Dimethyl oxalate; 1‐(6‐methoxypyridin‐3‐yl)ethan‐1‐one With hydrogenchloride; sodium methylate In methanol at 20 - 45℃; for 21.5h; Stage #2: With hydrogenchloride In methanol; chloroform; water Product distribution / selectivity; | 61% |
Dimethyl oxalate
glycine ethyl ester hydrochloride
dimethyloxalylglycine
Conditions | Yield |
---|---|
With triethylamine In methanol | 100% |
Dimethyl oxalate
4-bromo-2-fluoroacetophenone
Conditions | Yield |
---|---|
Stage #1: 4-bromo-2-fluoroacetophenone With lithium hexamethyldisilazane In tetrahydrofuran; 2-methyltetrahydrofuran at -78℃; for 0.25h; Stage #2: Dimethyl oxalate With hydrogenchloride In tetrahydrofuran; 2-methyltetrahydrofuran at -10℃; for 4h; | 100% |
Conditions | Yield |
---|---|
With ion-exchange resin Indion-130 In water at 75℃; for 1.5h; Reagent/catalyst; Autoclave; Sealed tube; Large scale; | 99.6% |
With sulfuric acid In methanol; water for 2h; Reflux; |
Conditions | Yield |
---|---|
With methanol; sodium Cooling with ice; | 99.5% |
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol at 80℃; for 0.000833333h; | 99.4% |
With hydrazine hydrate In methanol | 95% |
With hydrazine hydrate for 8h; Reflux; | 75% |
With hydrazine hydrate In methanol |
Conditions | Yield |
---|---|
With sodium methylate In methanol; diethyl ether at 20℃; | 99.2% |
Stage #1: Dimethyl oxalate; acetone With sodium methylate In methanol at 0 - 5℃; for 8h; Cooling with ice; Stage #2: With hydrogenchloride In water pH=2 - 3; | 90% |
With sodium methylate In methanol at 0℃; for 8h; | 90% |
Dimethyl oxalate
L-Phenylalaninol
(S)-N,N'-bis<1-(hydroxymethyl)-2-phenylethyl>ethanediamide
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.583333h; | 99% |
In methanol at 20℃; for 0.5h; | 99% |
In methanol at 20℃; for 0.0833333h; | 99% |
Dimethyl oxalate
(S)-2-amino-4-methylpentan-1-ol
(S,S)-N,N'-bis[1-(hydroxymethyl)-3-methylbutyl]ethanediamide
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.583333h; | 99% |
In methanol at 20℃; for 0.5h; | 99% |
In methanol at 20℃; for 0.0833333h; | 99% |
Conditions | Yield |
---|---|
With (o-PPh2C6H4NH2)[EtNH(CH2)2NHEt]RuCl2; hydrogen; sodium methylate In tetrahydrofuran; para-xylene at 5 - 100℃; under 7500.75 Torr; for 1.5h; Reagent/catalyst; Pressure; Temperature; Glovebox; | 99% |
With hydrogen In methanol at 219.84℃; under 18751.9 Torr; Temperature; Reagent/catalyst; Autoclave; | 32% |
With 1,1,1-tris(n-butylthiomethyl)ethane; hydrogen; zinc; Λ(+)-tris(pentane-2,5-dionato)ruthenium In methanol at 100℃; under 60004.8 Torr; for 69h; Kinetics; Product distribution; Further Variations:; Reagents; |
Dimethyl oxalate
(2R)-2-aminobutan-1-ol
N,N'-bis[(1R)-1-(hydroxymethyl)propyl]ethanediamide
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.583333h; | 99% |
In methanol at 20℃; for 0.5h; | 99% |
In methanol at 20℃; for 0.0833333h; | 99% |
Dimethyl oxalate
(S)-isoleucinol
N,N'-bis[(1S)-1-(S)-sec-butyl-2-hydroxyethyl]ethanediamide
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.5h; | 99% |
In methanol at 20℃; for 0.583333h; | 98% |
In methanol at 20℃; for 0.583333h; | 98% |
Dimethyl oxalate
N,N,N',N'-tetrabutyl-N''-ethylguanidine
N,N,N’,N‘-tetrabutyl-N''-ethyl-N''-methylguanidinium-methyl oxalate
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 72h; | 99% |
Conditions | Yield |
---|---|
In methanol at 0 - 20℃; for 4h; | 99% |
Dimethyl oxalate
(R)-2-methoxy-1-phenylethylamine
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.5h; Inert atmosphere; | 99% |
Dimethyl oxalate
1-phenylpropylamine
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.5h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 0℃; under 0 Torr; for 18h; Flow reactor; | 99% |
Conditions | Yield |
---|---|
Stage #1: Dimethyl oxalate; methanol With ammonia at 45℃; under 760.051 Torr; for 3h; Stage #2: With ammonia at 20 - 170℃; under 760.051 Torr; for 0.75 - 3h; | 98.6% |
Dimethyl oxalate
7-ethyl-3-methyl-4-nitroindole
Conditions | Yield |
---|---|
With potassium ethoxide In N,N-dimethyl-formamide Heating; | 98% |
Dimethyl oxalate
7-ethyl-3-methyl-6-nitroindole
1,3-dimethyl-7-ethyl-6-nitroindole
Conditions | Yield |
---|---|
With potassium ethoxide In N,N-dimethyl-formamide Heating; | 98% |
Conditions | Yield |
---|---|
With hydrogen In methanol at 179.84℃; under 18751.9 Torr; | 98% |
With C24H38Cl2N3PRu; hydrogen; sodium methylate In isopropyl alcohol at 100℃; under 38002.6 Torr; for 2h; Autoclave; | 97% |
With C24H38Cl2N3PRu; hydrogen; sodium methylate In isopropyl alcohol at 100℃; under 37503.8 Torr; for 2h; | 97% |
Dimethyl oxalate
O-methyldehydrozingerone
(5E)-methyl 6-(3,4-dimethoxyphenyl)-2-hydroxy-4-oxo-2-hexa-2,5-dienoate
Conditions | Yield |
---|---|
Stage #1: Dimethyl oxalate; O-methyldehydrozingerone With sodium methylate In tetrahydrofuran at 20℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water | 98% |
1-methyl-1H-imidazole
Dimethyl oxalate
N,N'-dimethylimidazolium-methyl oxalate
Conditions | Yield |
---|---|
In acetonitrile at 90℃; for 72h; | 98% |
Dimethyl oxalate
tributylphosphine
tributylmethylphosphonium-methyl oxalate
Conditions | Yield |
---|---|
In acetonitrile at 90℃; for 48h; | 98% |
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