Oxidation of 2,6-di-tert-butyl-4-methylphenol. The structure of C14H22O3
Journal of Organic Chemistry
By: G. R. Yohe, J. E. Dunbar, M.W. Lansford, R. L. Pedrotti, F. M. Scheidt, F. G. H. Lee, and E. C. Smith
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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.
Suggested Citation
Yohe, G.R., Dunbar, J., Lansford, M., Pedrotti, R.L., Scheidt, F.M., Lee, F.G., Smith, E.C., 1959, Oxidation of 2,6-di-tert-butyl-4-methylphenol. The structure of C14H22O3: Journal of Organic Chemistry, v. 24, no. 9, p. 1251-1256, https://doi.org/10.1021/jo01091a023.
| 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 |
| Publication Date | May 01, 2002 |
| 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 |