Oxidation of 2,6-di-tert-butyl-4-methylphenol. The structure of C14H22O3
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.
Citation Information
Publication Year | 1959 |
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Title | Oxidation of 2,6-di-tert-butyl-4-methylphenol. The structure of C14H22O3 |
DOI | 10.1021/jo01091a023 |
Authors | G. R. Yohe, J. E. Dunbar, M.W. Lansford, R. L. Pedrotti, F. M. Scheidt, F. G. H. Lee, E. C. Smith |
Publication Type | Article |
Publication Subtype | Journal Article |
Series Title | Journal of Organic Chemistry |
Index ID | 70010728 |
Record Source | USGS Publications Warehouse |