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Interaction of functionally-substituted 4-alkyl-2,6-di-tert-butylphenols with hydrohalic acids

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Abstract

Reactions of 4-alkyl-2,6-di-tert-butylphenols containing OH, SH, COOH, and COOMe groups in their para substituents with hydrogen chloride and hydrohalic acids were studied. One-step transformations of 2,6-di-tert-butyl-4-(ω-hydroxyalkyl)phenols to the corresponding 4-(ω-halogenoalkyl)phenols, as well as of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid and its esters to phloretic acid were proposed. 4-(3-Mercaptopropyl)phenol upon heating with conc. HBr undergoes condensation to 3-(4-hydroxyphenyl)propyl 4-(3-mercaptopropyl)phenyl sulfide as the main product.

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Authors and Affiliations

  1. Research Institute of Chemistry of Antioxidants, Novosibirsk State Pedagogical University, 28 ul. Vilyuiskaya, 630126, Novosibirsk, Russian Federation

    A. E. Prosenko, A. A. Skorobogatov, O. I. Dyubchenko, P. I. Pinko & N. V. Kandalintseva

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    M. M. Shakirov & L. M. Pokrovsky

Authors
  1. A. E. Prosenko
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  2. A. A. Skorobogatov
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  3. O. I. Dyubchenko
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  4. P. I. Pinko
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  5. N. V. Kandalintseva
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  6. M. M. Shakirov
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  7. L. M. Pokrovsky
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Correspondence to A. E. Prosenko.

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Dedicated to the memory of Academician N. N. Vorozhtsov on the 100th anniversary of his birth.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1078–1083, June, 2007.

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Prosenko, A.E., Skorobogatov, A.A., Dyubchenko, O.I. et al. Interaction of functionally-substituted 4-alkyl-2,6-di-tert-butylphenols with hydrohalic acids. Russ Chem Bull 56, 1119–1124 (2007). https://doi.org/10.1007/s11172-007-0169-y

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  • DOI: https://doi.org/10.1007/s11172-007-0169-y

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