Acetic Acid → HCID 13621301, compound

Participants

Reaction Steps

To a stirred solution of crude 1-benzoyl-2-bromomethyl-3-(dibromomethyl)benzene (2.3 g, 5 mmol) in glacial acetic acid (30 ml) was added sodium acetate (4.5 g, 55 mmol) in water (8 ml). The stirred mixture was heated to reflux temperature for sixteen hours, cooled and partitioned between diethylether (100 ml), ethyl acetate (20 ml) and 10% sodium carbonate solution (100 ml). Further solid sodium carbonate was added until effervescence ceased. The organic layer was washed with 10% sodium carbonate solution (30 ml) and brine (30 ml) and dried over sodium sulphate. Removal of the solvent under reduced pressure gave an oil (1.1 g) that was chromatographed (SiO2 (40 g) using (4:1) pentane:ethyl acetate as eluent). This gave 2-acetoxymethyl-3-benzoylbenzaldehyde (0.35 g, 22% from 1-benzoyl-2,3-dimethylbenzene).

Provenance & Evidence