to nitrotoluene, _p_-nitrobenzyl alcohol, _p_-nitrocinnamic acid
and similar compounds may be oxidized, but their cost is prohibitive
in comparison with that of the cheaper nitro hydrocarbon.

_p_-Nitrotoluene may be oxidized by means of strong nitric acid,[2]
chromic acid mixture,[3] or permanganates.[4] Electrolytic
oxidation[5] has also been proposed. The procedure given above
involves the use of chromic acid mixture, but, owing to a change
in the concentration of sulfuric acid, the time of reaction is greatly
shortened and the preparation is thus considerably improved.

[1] Ber. 8, 528, 536 (1875)

[2] Ann. 127, 137 (1863); 128, 257 (1863)

[3] Ann. 139, 335 (1866).

[4] J. Am. Chem. Soc. 41, 1575 (1919).

[5] R. P. 117, 129; Frdl. 6, 112.



XIV _ p_-NITROBENZYL CYANIDE

C6H5CH2CN + HNO3--> (_p_)NO2C6H4CH2CN + H2O

Prepared by G. R. ROBERTSON. Checked by ROGER ADAMS and H. O. CALVERY.

1. Procedure