Skip to main content
SpringerLink
Log in

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

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Battaini, J., De Carolis, M., Monzani, E., Tuczer, F., and Casella, L., Chem. Commun., 2003, p. 726. https://doi.org/10.1039/B212683D

  2. Chatterjee, A., Yadav, H.R., Choudhury, A.R., Ali, A., Singh, Y., and Ghosh, R., Polyhedron, 2018, vol. 141, p. 140. https://doi.org/10.1016/j.poly.2017.11.040

    Article  CAS  Google Scholar 

  3. Semenov, M.V, Komarov, A.G., Mikhailyuk, A.I., Litvintsev, I.Y., and Sapunov, V.N., Pet. Chem., 1995, vol. 35, p. 111.

    Google Scholar 

  4. Gonikberg, M.T., Khimicheskoe ravnovesie i skorost’ reaktsii pri vysokikh davleniyakh (Chemical Equilibrium and Reaction Rate at High Pressures), Moscow: Khimiya, 1969.

  5. Vol’eva, V.B., Ivanova, E.V., Batanov, I.A., and Ershov, V.V., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, vol. 35, p. 648. https://doi.org/10.1007/BF00953251

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 119334, Moscow, Russia

    V. B. Vol’eva, M. N. Ovsyannikova & L. N. Kurkovskaya

  2. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 119991, Moscow, Russia

    V. A. Zhorin

Authors
  1. V. B. Vol’eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Zhorin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. N. Ovsyannikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. N. Kurkovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Zhorin.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vol’eva, V.B., Zhorin, V.A., Ovsyannikova, M.N. et al. Solid-Phase ortho-Hydroxylation of 2,4-Di-tert-butylphenol and Its Derivatives. Russ J Org Chem 56, 350–352 (2020). https://doi.org/10.1134/S107042802001030X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042802001030X

Keywords:

Search

Navigation