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Organic Syntheses by Unknown
page 32 of 106 (30%)
2. Notes

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;
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