Organic Syntheses, CV 1, 240
[Benzocaine]
Submitted by Roger Adams and F. L. Cohen.
Checked by Henry Gilman and S. A. Harris.
1. Procedure
A solution of
19.5 g. (0.1 mole) of ethyl p-nitrobenzoate (Note
1) in
150 cc. of 95 per cent alcohol is placed in the reaction bottle of the catalytic reduction apparatus
(p. 61), and
0.2 g. of platinum oxide catalyst
(p. 463) is added. The mixture is shaken with
hydrogen until three molecular equivalents have been absorbed. The time required is about seven minutes. The
platinum is filtered off and the alcohol removed from the filtrate by distillation. The
ethyl p-aminobenzoate, recrystallized from about
40 cc. of ether, melts at
89–90°. The yield is
15–16.5 g. (
91–100 per cent of the theoretical amount).
2. Notes
1. The
ethyl p-nitrobenzoate should be freed from acid and recrystallized from alcohol until it melts at
57°.
3. Discussion
This preparation is referenced from:
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