Selective α-Monoalkylation of Phenylacetonitrile Using Alkali Metal Hydroxide Impregnated on Alumina

In the alkylation of phenylacetonitrile with alkyl halides, alkali metal hydroxides impregnated on alumina act as efficient bases for selective α-monoalkylation in benzene. It is proposed that the reaction may take place exclusively in the pore. The selectivity for α-monoalkylation is explained in terms of steric hindrance.