2-Hydroxy-4-Methoxybenzaldehyde → 2-Hydroxy-4-methoxybenzonitrile

Participants

Reaction Steps

2-Hydroxy-4-methoxybenzaldehyde (55 g; 0.36 mol), hydroxylamine hydrochloride (30 g; 0.43 mol) and sodium formate (34 g; 0.5 mol) were refluxed in formic acid (200 ml; 98-100%) for 1.25 h. The solution was then rapidly chilled in an ice bath, with stirring over 30 min. The resulting precipitate was separated by filtration and washed well with water. Following drying, in a desicator under vacuum, the title compound was obtained (45 g; 0.3 mol; 84% yield) as a brick-red solid, mp 169-171° C., rf (EtOAc) 0.43.

Provenance & Evidence