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Reactions of 3,5-di-tert-butyl-1,2-benzoquinone with mercapto carboxylic acids

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Abstract

Heating of an equimolar mixture of 3,5-di-tert-butyl-1,2-benzoquinone with thiosalicylic acid led to 2-[(4,6-di-tert-butyl-2,3-dihydroxyphenyl)thio]benzoic acid. In the case of β-mercaptopropionic acid, 2-[(4,6-di-tert-butyl-2,3-dihydroxyphenyl)thio]propionic acid was formed, which upon reflux in Ac2O was converted to 6,8-di-tert-butyl-9-hydroxy-3,4-dihydro-2H-1,5benzoxathiepin-2-one.

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344090, Rostov on Don, Russian Federation

    L. Yu. Ukhin, L. V. Belousova, D. V. Alekseenko, G. S. Borodkin & L. N. Etmetchenko

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    K. Yu. Suponitsky

  3. Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova, 344006, Rostov on Don, Russian Federation

    E. N. Shepelenko

Authors
  1. L. Yu. Ukhin
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  2. K. Yu. Suponitsky
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  3. E. N. Shepelenko
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  4. L. V. Belousova
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  5. D. V. Alekseenko
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  6. G. S. Borodkin
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  7. L. N. Etmetchenko
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Correspondence to L. Yu. Ukhin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0727—0730, March, 2016.

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Ukhin, L.Y., Suponitsky, K.Y., Shepelenko, E.N. et al. Reactions of 3,5-di-tert-butyl-1,2-benzoquinone with mercapto carboxylic acids. Russ Chem Bull 65, 727–730 (2016). https://doi.org/10.1007/s11172-016-1363-6

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  • DOI: https://doi.org/10.1007/s11172-016-1363-6

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