4-Chlorobenzaldehyde → anti-p-Chlorobenzaldoxime

Participants

Reaction Steps

To a suspension of 4-chlorobenzaldehyde (25.0 g, 178 mmol) and hydroxylamine hydrochloride (13.7 g, 198 mmol) in ethanol (14.2 mL) and water (42.9 mL) was added ice (82.4 g). Then a solution of sodium hydroxide (18.1 g, 455 mmol) in water (21.4 mL) was added dropwise within a 10 min period (temperature rises from −8° C. to +7° C.) whereupon most of the solid dissolves. After 30 min stirring at room temperature a white solid precipitated and the resulting mixture was then diluted with water and acidified with HCl (4 N). The white precipitate was then filtered off, washed with water and dried under high vacuum to afford the title compound (27.0 g, 97%) which was obtained as an off white solid. MS: m/e=155.1 [M]+.

Provenance & Evidence