The benzyl cyanide, prepared according to the procedure as outlined,
is collected over a 5'0 range. It varies in appearance
from a colorless to a straw-colored liquid and often develops
appreciable color upon standing. For a product of special purity,
it should be redistilled under diminished pressure and collected
over a 1-2'0 range. For most purposes, such as the preparation
of phenylacetic acid or ester, the fraction boiling 135-140'0/38 mm.
is perfectly satisfactory. 3. Other Methods of Preparation

Benzyl cyanide occurs naturally in certain oils.[1] The only feasible
method of preparing it that has been described in the literature is
the one in which alcoholic potassium cyanide and benzyl chloride[2]
are employed. The cheaper sodium cyanide is just as satisfactory
as the potassium cyanide and therefore is the best material to use.
Gomberg has recently prepared benzyl cyanide from benzyl chloride
and an aqueous solution of sodium cyanide.[3]


[1] Ber. 7, 519, 1293 (1874); 32, 2337 (1899)

[2] Ann. 96, 247 (1855); Ber. 3, 198 (1870); 14, 1645
(1881); 19, 1950 (1886).

[3] J. Am. Chem. Soc. 42, 2059 (1920).



IV