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Potassium and sodium 2,6-di-tert-butylphenoxides and their properties

Potassium and sodium 2,6-di-tert-butylphenoxides and their properties The crucial factor of the reaction of 2,6-di-tert-butylphenol with alkali hydroxides is temperature, depending on which two types of potassium or sodium 2,6-di-tert-butylphenoxides are formed. These types exhibit different catalytic activity in the alkylation of 2,6-di-tert-butylphenol with methyl acrylate. More active forms of 2,6-But 2C6H3OK or 2,6-But 2C6H3ONa are synthesized at temperatures higher than 160 °C and are predominantly the monomers, which dimerize on cooling. The data of 1H NMR, electronic, and IR spectra for the corresponding forms of 2,6-But 2C6H3OK and 2,6-But 2C6H3ONa isolated in the individual state are in agreement with cyclohexadienone structure. In DMSO or DMF, the dimeric forms of 2,6-di-tert-butylphenoxides react with methyl acrylate to form methyl 3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate in 64–92% yield. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Russian Chemical Bulletin Springer Journals

Potassium and sodium 2,6-di-tert-butylphenoxides and their properties

Russian Chemical Bulletin , Volume 55 (12) – Dec 1, 2006

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References (4)

Publisher
Springer Journals
Copyright
Copyright © 2006 by Springer Science+Business Media, Inc.
Subject
Chemistry; Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry
ISSN
1066-5285
eISSN
1573-9171
DOI
10.1007/s11172-006-0575-6
Publisher site
See Article on Publisher Site

Abstract

The crucial factor of the reaction of 2,6-di-tert-butylphenol with alkali hydroxides is temperature, depending on which two types of potassium or sodium 2,6-di-tert-butylphenoxides are formed. These types exhibit different catalytic activity in the alkylation of 2,6-di-tert-butylphenol with methyl acrylate. More active forms of 2,6-But 2C6H3OK or 2,6-But 2C6H3ONa are synthesized at temperatures higher than 160 °C and are predominantly the monomers, which dimerize on cooling. The data of 1H NMR, electronic, and IR spectra for the corresponding forms of 2,6-But 2C6H3OK and 2,6-But 2C6H3ONa isolated in the individual state are in agreement with cyclohexadienone structure. In DMSO or DMF, the dimeric forms of 2,6-di-tert-butylphenoxides react with methyl acrylate to form methyl 3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate in 64–92% yield.

Journal

Russian Chemical BulletinSpringer Journals

Published: Dec 1, 2006

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