Hydroxyamine hydrochloride → Ethyl 6-hydroxyimino-6-(2-naphthyl)hexanoate

Participants

Reaction Steps

An ethanolic solution (150 ml) of ethyl 6-oxo-6-(2-naphthyl)hexanoate (15 g) was added to an aqueous solution (42 ml) of hydroxylamine hydrochloride (4.8 g) and sodium acetate (5.7 g) and the mixture was refluxed for 2 hours. The ethanol was then distilled off under reduced pressure and the residue was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried and the solvent was distilled off. The crude residue was purified by silica gel column chromatography (hexane-ethyl acetate =10:1) to provide ethyl 6-hydroxyimino-6-(2-naphthyl)hexanoate (19 g).

Provenance & Evidence