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

• Published in: Russian journal of organic chemistry Vol. 56; no. 2; pp. 350 - 352
• Main Authors: Vol’eva, V. B., Zhorin, V. A., Ovsyannikova, M. N., Kurkovskaya, L. N.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-04-2020; Springer Nature B.V
• Subjects: Anvils; Catechol; Chemistry; Chemistry and Materials Science; Copper oxides; Derivatives; Hydroxylation; Organic Chemistry; Phenols; Shear deformation; Solid phases; oxidative coupling; shear deformation; butylphenol; butylcatechol; hydroxylation; cupric oxide; cuprous oxide; Bridgman anvils; 3,5-di; 2,4-di; high pressure; solid-phase reactions
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S107042802001030X

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.