Hydrogen Peroxide → 4-Acetylbutyric acid

Participants

Reaction Conditions

Reaction Steps

Ozone was passed through a solution of 2.0 gms of 3-methyl-2-cyclohexenone at -78° C. for 30 minutes. The mixture was warmed to -20° C. and treated with a solution of 3.0 g of 30% hydrogen peroxide in 3.0 g of 50% NaOH. A drop of Adogen 464 was added and the two phase mixture was stirred vigorously for 1 hour. The aqueous phase was separated and acidified then extracted with ether. Removal of the ether afforded 1.12 g (48%) of 5-keto-hexanoic acid. The identity of the acid was confirmed by comparing the IR spectra of its methyl ester to the known spectra of the same compound.

Provenance & Evidence