Solid-Phase ortho-Hydroxylation of 2,4-Di-tert-butylphenol and Its Derivatives

Direct phenol–catechol conversion has been realized as a result of the solid-phase reaction of 2,4-di- tert -butylphenol with cuprous oxide under high pressure and shear deformation on the Bridgman anvils. The yield of 3,5-di- tert -butylcatechol in this reaction was about 85%. When cupric oxide was...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-04, Vol.56 (2), p.350-352
Main Authors: Vol’eva, V. B., Zhorin, V. A., Ovsyannikova, M. N., Kurkovskaya, L. N.
Format: Article
Language:English
Subjects:
Anvils
Catechol
Chemistry
Chemistry and Materials Science
Copper oxides
Derivatives
Hydroxylation
Organic Chemistry
Phenols
Shear deformation
Solid phases
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Summary:Direct phenol–catechol conversion has been realized as a result of the solid-phase reaction of 2,4-di- tert -butylphenol with cuprous oxide under high pressure and shear deformation on the Bridgman anvils. The yield of 3,5-di- tert -butylcatechol in this reaction was about 85%. When cupric oxide was used in the solid-phase process, oxidative coupling of the starting phenol took place, resulting in quantitative formation of tetra- tert -butyl- ortho -bisphenol. The reaction of 6-substituted derivatives of 2,4-di- tert -butylphenol with cuprous oxide was used as an example to demonstrate the possibility of substitutive ortho -hydroxylation yielding 7–20% of pyrocatechols.
ISSN:1070-4280
1608-3393
DOI:10.1134/S107042802001030X