USGS Science⌕ Search
Home/Archive/USGS

USGS · 70010728

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

G. R. Yohe·J. E. Dunbar·M.W. Lansford·R. L. Pedrotti·F. M. Scheidt·F. G. H. Lee·E. C. Smith
View original source ↗Export metadata ↓

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.

Explore related subjects

Journal of Organic ChemistryArticle

Keep this discovery

Explore connections, maps & timelines

BibTeXRIS

G. R. Yohe, J. E. Dunbar, M.W. Lansford, R. L. Pedrotti, F. M. Scheidt, F. G. H. Lee, E. C. Smith. 2002-05-01. Oxidation of 2,6-di-tert-butyl-4-methylphenol. The structure of C14H22O3. https://doi.org/10.1021/jo01091a023

Cite the original work for its findings. Save a collection to share your selection of sources.

KEEP EXPLORING

Related USGS reports

USGS2002

Direct conversion of terpenylalkanolamines to ethylidyne N -nitroso compounds

A series of mono- and diterpenylalkanolamines bearing isopropylidene functionality on the terpene group was reacted with sodium nitrite in aqueous acetic acid to yield ethylidyne N -nitroso analogues. The key feature of this direct conversion involved initial N-nitrosation followed by apparent elimination of a "CH 4 " unit (not necessarily methane) from the isopropylidene double bond. The product distribution data for ethylidyne nitrosamines derived from tertiary terpenyl alkanolamines reflect the conformational outcome of the nitrosative dealkylation process. For β , γ -unsaturated allylic diterpenylethanolamines, electronic effects appeared to be important for controlling the product distribution of ethylidyne nitrosamines in light of the highly selective α -cleavage observed in the nitrosation reactions.

Journal of Organic Chemistry↗
USGS2002

Aromatic fluorine compounds. XI. Replacement of chlorine by fluorine in halopyridines

The α -halogenated pyridines react with potassium fluoride in various solvents to give replacement of the α -halogen by fluorine. A 50% yield of 2-fluoropyridine was obtained from 2-chloropyridine by heating with potassium fluoride in dimethyl sulfone or tetramethylene sulfone for twenty-one days; 2-bromopyridine gave a similar yield with a heating period of only seven days. The α -halogens of the polyhalopyridines undergo the exchange reaction more readily than do the halogens of the α -monohalopyridines. The proposed structures of the fluoropyridines are supported by alternate syntheses and by n.m.r. studies.

Journal of Organic Chemistry↗