4-Chlorobenzaldehyde → anti-p-Chlorobenzaldoxime

To a suspension of 4-chlorobenzaldehyde (25.0 g, 178 mmol) and hydroxylamine hydrochloride (13.7 g, 198 mmol) in ethanol (14.1 mL) and water (42.9 mL) was added ice (82 g). Then a solution of sodium hydroxide (18.1 g, 454 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 (EI): 155.1 [M]+.

1. dissolutiondissolves
2. customprecipitated
3. additionthe resulting mixture was then diluted with water
4. filtrationThe white precipitate was then filtered off
5. washwashed with water
6. customdried under high vacuum

ORD record

ord-377a2f4c26174aa39729268143da9ce0

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604062B2