Potassium Cyanide → 4-(Cyanomethyl)benzoic acid

Participants

Reaction Steps

A suspension of 4-bromomethylbenzoic acid (25.26 g, 0.12 mol) and KCN (20 g, 0.31 mol) in 5:7 H2O/EtOH (60 mL) was heated to 75°-80° C. for four hours. The cooled reaction was partially concentrated, H2O added, and extracted 1× with EtOAc. After acidification of the aqueous layer, the resulting precipitate was filtered and washed well with H2O to yield 13.6 g; 4 EtOAc extractions of the filtrate yielded an additional 2.7 g. Recrystallization of the combined solids from H2O/EtOH using activated charcoal and filtering through Celite afforded 15.20 g of 4-cyanomethylbenzoic acid.

Provenance & Evidence