Sodium Cyanide → 4-Hydroxybenzyl cyanide

Participants

Reaction Steps

A solution of p-chloromethyl phenol in acetonitrile (Example 12) was reacted with equimolar sodium cyanide in excess methanol (800 parts methanol/mole sodium cyanide) and the reaction mixture was refluxed for one hour. The oil after solvent evaporation (washed as in Experiment 18) was fractionated to yield 45% of α-cyano-p-cresol (b.p. 50°-155°/1 mm. of mercury; M.P. 68°-70°). Infrared spectra confirmed the identity of the product.

Provenance & Evidence