Sodium Cyanide → (3-Benzoylphenyl)ethanenitrile

Participants

Reaction Steps

m-(Bromomethyl)benzophenone is reacted with sodium cyanide to form (m-benzoylphenyl)acetonitrile which is reacted with diethyl carbonate in the presence of sodium ethoxide to form sodium salt of ethyl alpha-cyano(m-benzoylphenyl)acetate. The sodium salt is reacted with methyl iodide to obtain ethyl alpha-cyano-alpha-(m-benzoylphenyl)propionate. The resulting ester is hydrolyzed and then subjected to decarboxylation to form alpha-(m-benzoylphenyl)propionitrile. Alkaline hydrolysis of alpha-(m-benzoylphenyl)propionitrile affords alpha-(m-benzoylphenyl)propionic acid. (For details, see British Patent No. 1,164,585).

Provenance & Evidence