Ethyl formate → 2-Formyl-2-phenylacetonitrile

Participants

Reaction Steps

To a suspension of sodium methoxide (10.8 g) in benzene (300 ml) is added dropwise with stirring a mixture of ethyl formate (16.28 g) and phenylacetonitrile (23.4 g) under ice cooling. After 30 minutes, the ice bath is taken off. After reacting for 3 hours, ice water is added to the reaction mixture, and the aqueous layer is separated. The organic layer is washed with 0.5 N sodium hydroxide solution (100 ml×3), and the aqueous layer and the washings are combined and adjusted to pH 3-4 with conc. hydrochloric acid. The mixture is stirred under ice cooling for 20 minutes, and the resulting precipitate is separated by filtration and washed with water to give α-formylphenylacetonitrile (21.13 g). The product is used in the subsequent procedure without further purification.

Provenance & Evidence