Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
Formylation of Phenols with Electron-withdrawing Groups in Strong Acids. Synthesis of Substituted Salicylaldehydes
YUJI SUZUKIHIROSHI TAKAHASHI
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1983 Volume 31 Issue 5 Pages 1751-1753

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Abstract

Salicylaldehydes with electron-withdrawing groups, i.e., 2-hydroxy-5-nitrobenzaldehyde (2a), methyl 3-formyl-4-hydroxybenzoate (2b), methyl 5-chloro-3-formyl-2-hydroxybenzoate (2c), 3, 5-dichloro-2-hydroxybenzaldehyde (2d), 5-cyano-2-hydroxybenzaldehyde (2e), and 5-fluoro-2-hydroxybenzaldehyde (2f), were synthesized by the formylation of the corresponding phenols (1a-f) with hexamethylenetetramine in 75% polyphosphoric acid, methanesulfonic acid, or trifluoroacetic acid. The yields of these reactions were better than those of the Duff reaction.

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