Chemical Synthesis of α-Formylphenylacetic Acid, the Postulated Precursor of Tropic Acid
1981 ◽
Vol 36
(7-8)
◽
pp. 611-614
◽
Keyword(s):
Abstract a-Formylphenylacetic Acid, Phenylmalonic Semialdehyde, Tropic Acid Biosynthesis a-Formylphenylacetic acid, the postulated immediate precursor of tropic acid, has been synthesized by deacetalization of a-diethoxymethylphenylacetic acid in the presence of silica gel. The compound was reasonably stable in organic solution. In aqueous media, however, a pronounced lability of this semialdehyde was observed at various pH-values (t/2 = 4.5 min at pH 7.4). It is thus very unlikely that this compound can be employed successfully in biosynthetic studies.