Ethanol → 2-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde oxime

Participants

Reaction Steps

A mixture of 2.25 g (7.72 mmol) of 2-hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde and 0.59 g (8.49 mmol) of hydroxylamine hydrochloride in 15 ml of 1:1:1 tetrahydrofuran:ethanol:water was cooled in an ice-water bath. Sodium bicarbonate (0.78 g, 9.26 mmol) was added in small portions over 15 minutes. After stirring overnight at ambient temperature, water (25 ml) was added and the solid was filtered and dried. There was obtained 2.00 g (6.52 mmol, 85%) of 2-hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde oxime as a white solid after crystallization from cyclohexane mp 175°-177° C.

Provenance & Evidence