The benzyl cyanide can be most conveniently prepared according to the directions in preparation III (p. 9); the product which boils over a 5'0 range should be used.
In washing the layer of ethyl phenylacetate with sodium carbonate it is sometimes advisable to add a certain amount of sodium chloride so that the ester will separate more readily.
The product obtained is water-clear and practically colorless. Although the product is collected over a 5'0 range, most of the liquid is found to boil over a 1'0 range, if distilled slowly without superheating.
The boiling point of ethyl phenylacetate is near that of benzyl cyanide. However, a Kjeldahl analysis of the product shows that only a trace of nitrogen compounds is present.
3. Other Methods of Preparation
Ethyl phenylacetate may be prepared by the treatment of benzyl cyanide with alcohol and hydrochloric acid gas.[1] It is much more convenient in the laboratory, however, to use sulfuric acid in place of hydrochloric acid; in fact, the yields obtained are better than those recorded in the literature. This ester may also be made by the esterification of phenylacetic acid with hydrochloric acid and alcohol;[2] or with alcohol and sulfuric acid;[3] the following less important methods of preparation may be mentioned; the action of benzyl magnesium chloride upon ethyl chlorocarbonate,[4] and the action of copper on a mixture of bromobenzene and ethyl chloroacetate at 180'0.[5]
[1] Ber. 20, 592 (1887); Ann. 296, 361 (1897)
[2] Ber. 2, 208 (1869).
[3] Ann. 296, 2, footnote (1897); Compt. rend. 152, 1855 (1911).
[4] Ber. 36, 3088 (1903).