Oxidation of 2,6-di-tert-butyl-4-methylphenol. The structure of C14H22O3

Journal of Organic Chemistry
By: , and 

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Abstract

The acidic compound C14H22O3, previously reported without assignment of structure as an oxidation product of 2,6-di-tert-butyl-4-methylphenol, is now believed to be DL-trans-5,6-di-tert-butyl-2-hydroxy-1,4-diketo-2-cyclohexene (I). Chemical properties are described and infrared spectra are presented in support of this structure. This structure is of interest in relation to the problem of the existence of o-di-tert-alkylbenzene derivatives. The relatively easy racemization of optically active I suggests that its completely enolized form, 5,6-di-tert-butyl-1,2,4-trihydroxybenzene, is capable of transitory existence.

Additional publication details

Publication type Article
Publication Subtype Journal Article
Title Oxidation of 2,6-di-tert-butyl-4-methylphenol. The structure of C14H22O3
Series title Journal of Organic Chemistry
DOI 10.1021/jo01091a023
Volume 24
Issue 9
Year Published 1959
Language English
Publisher American Chemical Society
Larger Work Type Article
Larger Work Subtype Journal Article
Larger Work Title Journal of Organic Chemistry
First page 1251
Last page 1256
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