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Base catalyzed acylative decarboxylation. Part III. Acylation of homophthalic acid
Author(s) -
Smith Grant Gill,
Delong Carol Witte,
Wetzel William H.,
Muralidharan V. P.
Publication year - 1967
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570040407
Subject(s) - chemistry , decarboxylation , acylation , acetic anhydride , isocoumarin , catalysis , acetic acid , organic chemistry , isocoumarins , medicinal chemistry
Homophthalic acid (I) reacts with acetic anhydride in the presence of base to form the expected product, o ‐carboxyphenylacetone (III). Besides III, three other new products were formed, namely, 3‐methyl‐4‐carboxyisocoumarin (II), 4‐acetyl‐3‐methylisocoumarin (IV) and 8‐acetyl‐7‐methylnaphtho[1,2‐ c ]isocoumarin. A mechanism for the formation of these compounds is presented. The presence of 3‐methyl‐4‐carboxyisocoumarin (II) supports an earlier suggestion (1) that acylation can occur prior to and without decarboxylation, which has been a point of concern in this reaction.