Org. Synth. 1928, 8, 66
Submitted by Roger Adams and F. L. Cohen.
Checked by Henry Gilman and S. A. Harris.
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.
per cent of the theoretical amount).
The ethyl p-nitrobenzoate
should be freed from acid and recrystallized from alcohol until it melts at 57°
can be prepared by the esterification of p-aminobenzoic acid
and by the reduction of ethyl p-nitrobenzoate
with ammonium sulfide
and with tin and alcoholic hydrochloric acid
Although the reducing agent used commercially is generally iron
and water in the presence of a little acid, the catalytic reduction procedure described is by far the most convenient for the laboratory. The catalytic reduction of ethyl p-nitrobenzoate
has been described in the literature.5
This preparation is referenced from:
Chemical Abstracts Nomenclature (Collective Index Number);
hydrochloric acid (7647-01-0)
aminobenzoic acid (118-92-3)
Ethyl p-aminobenzoate (94-09-7)
ethyl p-nitrobenzoate (99-77-4)
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