Acetic Acid → HCID 22277855, compound

Participants

Reaction Steps

A solution of 3,5-dichloro-4-hydroxybenzaldehyde (2.00 g, 10.5 mmol) and O-benzylhydroxylamine hydrochloride (1.84 g, 11.55 mmol) in 5 ml of pyridine was stirred for 2 h. All volatiles were removed in vacuo and the resulting imine intermediate was treated with sodium cyanoborohydride (1.98 g, 31.5 mmol) in 10 ml of glacial acetic acid for 4 h. The reaction mixture was quenched with water and neutralized with sodium bicarbonate powder, extracted with ethyl acetate and dried (sodium sulfate). Removal of all volatiles in vacuo afforded the crude 4-(Benzyloxyamino-methyl)-2,6-dichlorophenol (4.02 g) as a light yellow oil (M+1=298). This was converted to the title compound using the method described in example 1c (2.01 g, 59%) as a thick colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 7.38 (m, 3H), 7.28 (m, 2H), 7.19 (s, 2H), 5.97 (s, 1H), 4.78 (s, 2H), 4.55 (s, 2H). M+1=326.

Provenance & Evidence