Carbon Dioxide → 2-Ethyl-4-methoxy-4-oxobutanoate
Reaction equation
[C:1](=[O:3])=[O:2].C([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]C)=[O:11])=O.[C:14]([O:23][CH3:24])(=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18]C([O-])=O>>[CH3:6][CH:7]([CH2:8][CH2:9][C:10]([O-:12])=[O:11])[C:1]([O:3][CH3:14])=[O:2].[CH2:17]([CH:16]([C:1]([O-:3])=[O:2])[CH2:15][C:14]([O:23][CH3:24])=[O:22])[CH3:18]Participants
Procedure
The cleavage is advantageously carried out in the presence of molecular oxygen or of a gas which contains molecular oxygen as well as an inert gas, such as nitrogen, carbon dioxide, argon or steam. A molar ratio of formylvaleric ester to molecular oxygen of from 1:0.05 to 1:3, in particular from 1:0.2 to 1:1.5, e.g. from 1:0.5 to 1:1.25, is preferably used. This increases the catalyst life and in particular the yield of pentenoic esters. The concomitant use of molecular oxygen was not indicated, since it was known from European Patent 131,860 that methyl 5-formylvalerate is oxidized to monomethyl adipate in a yield of 96% by molecular oxygen at as low as 50° C., and it was therefore to be expected that 4- and 3-formylvaleric esters would be oxidized in a similar manner to give monomethyl 2-methylglutarate and monomethyl 3-ethylsuccinate.
Workup
- temperatureThis increases the catalyst life
Sources & evidence
- ORD record
- ord-76d87c4afdf24403b612a2e34cd27c40
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04879406
Reaction notes
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