Vanillin → 4-Hydroxy-3-methoxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a 3-necked 500 mL round bottom flask equipped with a mechanical stirrer and a condenser, 3-methoxy-4-hydroxy benzoaldehyde (50.2 g, 0.33 mole), hydroxylamine hydrochloride (25.5 g, 0.37 mole), and N,N′-dimethylformamide (40 mL) were successively added at 25° C., followed by heating in an oil bath at 140° C. for 1 hour. The reaction mixture was allowed to cool to 85° C., and water (250 mL) was added to yield 3-methoxy-4-hydroxybenzonitrile. The reaction mixture was further cooled to 10° C. for a complete precipitation, and the resulting solid was then isolated by filtration and dried under reduced pressure to yield a product as an off-white solid with a yield of 95% and a purity of higher than 99% as indicated by HPLC analysis.

Provenance & Evidence