Benzaldehyde → m-Formylbenzonitrile

Participants

Reaction Steps

A compound having the above formula was prepared in the following manner. A solution of m-cyanobenzaldehyde was prepared by dissolving 2.0 gms. (15.2 mmoles) of the benzaldehyde along with 2.98 gms. (45.8 mmoles) of NaN3 and 2.9 gms. (21.1 mmoles) of Et3N.HCl, all of which were dissolved in 50 ml. of 1-methyl-2-pyrrolidinone. The reaction mixture was refluxed under argon. After 1 hour and 45 minutes the reaction mixture was cooled to room temperature and poured into 200 ml. of water and acidified with 10% hydrochloric acid. The reaction mixture was extracted with successive ethyl acetate washes. The ethyl acetate extracts were combined and washed with brine and dried over magnesium sulfate. The ethyl acetate extract was chromatographed through silica gel, yielding 0.3 gms. of the product having the above formula as a white solid.

Provenance & Evidence