Sodium Chloride → 4-Hydroxybenzyl cyanide

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (4.0 g.) and sodium cyanide (5.0 g.) are added to a stirred suspension of sodium p-hydroxymandelate monohydrate (19 g. of 89% w/w material, the impurity being sodium chloride) in N,N-dimethylformamide (100 ml.) and the mixture is stirred and heated at 135° C. for 4 hours and then cooled. Formic acid (7.7 ml.) and water (200 ml.) are added and the mixture is extracted twice with methyl isobutyl ketone (100 ml. and 75 ml.). The combined extracts are washed twice with water (40 ml. each time) and are then concentrated by evaporation. There is thus obtained a solution of p-hydroxybenzyl cyanide in methyl isobutyl ketone which is suitable for conversion to p-hydroxyphenylacetamide without further purification.

Provenance & Evidence