Alkylation of pyrocatechol in tert-butyl alcohol-sulfuric acid-benzene

Alkylation of pyrocatechol with tert -butyl alcohol in benzene in the presence of sulfuric acid gave 3,5-di- tert -butylbenzene-1,2-diol in a higher yield than in analogous reaction with tert -butyl alcohol. This result was rationalized by reduction of inhibitory effect of liberated water, formation...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2011-09, Vol.47 (9), p.1310-1312
Main Authors: Vol’eva, V. B., Prokof’eva, T. I., Belostotskaya, I. S., Komissarova, N. L., Gorbunov, D. B., Kurkovskaya, L. N.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Alkylation of pyrocatechol with tert -butyl alcohol in benzene in the presence of sulfuric acid gave 3,5-di- tert -butylbenzene-1,2-diol in a higher yield than in analogous reaction with tert -butyl alcohol. This result was rationalized by reduction of inhibitory effect of liberated water, formation of heterogeneous system, and occurrence of the alkylation process in nonpolar organic phase. Intermediate products were identified and found to undergo intra- and intermolecular tert -butyl group transfer with formation of more stable 3,5-di- tert butylbenzene-1,2-diol. The formation of p -di- tert -butylbenzene indicated participation of benzene in crossalkylation processes.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428011090089