The standard method of preparation of phenylacetic acid is by the
hydrolysis of benzyl cyanide with either alkali[1a] or acid.[2a] The acid
hydrolysis runs by far the more smoothly and so was the only one studied.
There are numerous other ways in which phenylacetic acid has been formed,
but none of them is of practical importance for its preparation.
These methods include the following: the action of water on phenyl
ketene;[3a] the hydrolysis and subsequent oxidation of the product
between benzaldehyde and hippuric acid;[1] the reduction of mandelic
acid;[2] the reduction of benzoylformic acid with hydriodic acid
and phosphorus;[3] the hydrolysis of benzyl glyoxalidone;[4]
the fusion of atropic acid with potassium hydroxide;[5] the action
of alcoholic potash upon chlorophenylacetylene;[6] the action
of benzoyl peroxide upon phenylacetylene;[7] the alkaline hydrolysis
of triphenylphloroglucinol;[8] the action of ammonium sulfide
upon acetophenone;[9] the heating of phenylmalonic acid;[10]
the hydrolysis of phenylacetoacetic ester;[11] the action of hydriodic
acid upon mandelonitrile.[12]
[1a] Ann. 96, 247 (1855); Ber. 14, 1645 (1881); Compt.
rend. 151, 236 (1910).
[2a] Ber. 19, 1950 (1886).
[3a] Ber. 44, 537 (1911).
[1] Ann. 370, 371 (1909)a
[2] Chem. (2) 1, 443 (1865); Ber. 14, 239 (1881).
[3] Ber. 10, 847 (1877)
[4] J. prakt. Chem. (2) 82, 52, 58 (1910).
[5] Ann. 148, 242 (1868).
[6] Ann. 308, 318 (1899).
[7] J. Russ. Phys. Chem. Soc. 42, 1387 (1910); Chem. Zentr.
1911 (I) 1279.
[8] Ann. 378, 263 (1911).
[9 Ber. 21, 534 (1888); J. prakt. Chem. (2) 81, 384 (1910).
[10] Ber. 27, (1894).
[11] Ber. 31, 3163 (1898)
[12] Inaugural Dissertation of A. Kohler (1909), Univ. of Bern.