L. D. Smirnov, V. I. Kuz’min, L. Mikhailova
Aug 1, 1971
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Journal
Russian Chemical Bulletin
Abstract
1. A study was made of the sulfonation of the 2-phenyl-, 2-(4′-alkylphenyl)-2-(4′-methoxyphenyl)-, 2-(3′,4′-dimethoxyphenyl)-, and 2-(4′-hydroxyphenyl)-3-hydroxypyridines. 2. In the case of 2-phenyl-3-hydroxypyridine the substitution was directed to the p-position of the phenyl ring, whereas in the p-aryl-substituted 3-hydroxypyridines the sulfo group substitutes in the mposition of the phenyl ring. 3. A comparison of the conditions for the sulfonation of benzene and 2-phenyl-3-hydroxypyridine discloses that the presence of a heterocyclic ring as a substituent in the phenyl ring lowers the reactivity of the latter in sulfonation reactions. 4. The insertion of alkyl groups (with the exception of tert-butyl), methoxy, and hydroxy groups in the phenyl ring facilitates sulfonation. 5. 2-(3′-Hydroxy-4′-alkylphenyl)-3-hydroxypyridines were synthesized by the alkaline fusion of sulfo acids of the 2-(4′-alkylphenyl)-3-hydroxypyridine series.