BENZYL CYANIDE

C6H5CH2Cl + NaCN--> C6H5CH2CN + NaCl

Prepared by ROGER ADAMS and A. F. THAL Checked by O. KAMM and
A. O. MATTHEWS.

1. Procedure

IN a 5-l. round-bottom flask, fitted with a stopper holding
a reflux condenser and separatory funnel, are placed 500 g.
of powdered sodium cyanide (96-98 per cent pure) and 450 cc.
of water. The mixture is warmed on a water bath in order
to dissolve most of the sodium cyanide, and then 1 kg.
of benzyl chloride (b. p. 170-180'0) mixed with 1 kg.
of alcohol is run in through the separatory funnel in the course
of one-half to three-quarters of an hour. The mixture is then
heated with a reflux condenser on the steam bath for four hours,
cooled and filtered with suction to remove most of the sodium chloride.
It is well to wash the filtered salt with a small portion of
alcohol in order to remove any benzyl cyanide which may have been
mechanically held. The flask is now fitted with a condenser,
and as much alcohol as possible is distilled off on the steam bath.
The residual liquid is cooled, filtered if necessary, and the layer
of benzyl cyanide separated. This crude benzyl cyanide is now
placed in a Claisen distilling flask and distilled _in vacuo_,
the water and alcohol coming over first, and finally the cyanide.
It is advantageous to use a fractionating column or, better still,
a Claisen flask with a modified side-arm[1] (Vol. I, p.