Methanol → methyl (4E)-4-hydroxyimino-4-phenylbutanoate

Participants

Reaction Steps

A mixture of methyl 3-benzoylpropionate (15.0 9), hydroxylamine hydrochloride (6.50 g), sodium acetate (9.60 g) and methanol (150 ml) was heated under reflux for 8 hours. The reaction mixture was concentrated, water was added to the residue and the mixture was extracted with ethyl acetate The ethyl acetate layer was washed with water, dried (over MgSO4) and concentrated. The residue was subjected to a silica gel column chromatography and, from an eluate with ethyl acetate-hexane (1:3, volume ratio), methyl (E)-4-hydroxyimino-4-phenylbutyrate (14.7 g; yield: 91%) was obtained as an oily product.

Provenance & Evidence