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Deacylation of aromatic ketones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The methyl esters of β-(2,5-di-tert-butyl-3-thenoyl)propionic and γ-(2,5-di-tert-butyl-3-thenoyl)butyric acids are deacylated by prolonged refluxing with a mixture of hydrochloric and formic acids to form di-tert-butylthiophene and aliphatic dicarboxylic acids (succinic and glutaric acids, respectively). The same process also occurs on heating 2,5-di-tert-butyl-3-acetylthiophene under the same conditions. Practically no deacylation occurs on refluxing these thiophene derivatives with hydrochloric acid alone or with a mixture of hydrochloric acid and acetic acid. Attempts to deacylate methyl β-(2,5-diethyl-3-thenoyl)propionate were unsuccessful. Assumptions regarding the peculiarities of deacylation in the 2,5-dialkyl-3-acylthiophene series associated with the geometry of the thiophene ring are expressed.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    B. P. Fabrichnyi, I. F. Shalavina, S. M. Kostrova & Ya. L. Gol'dfarb

Authors
  1. B. P. Fabrichnyi
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  2. I. F. Shalavina
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  3. S. M. Kostrova
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  4. Ya. L. Gol'dfarb
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 181–183, February, 1971.

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Fabrichnyi, B.P., Shalavina, I.F., Kostrova, S.M. et al. Deacylation of aromatic ketones. Chem Heterocycl Compd 7, 165–167 (1971). https://doi.org/10.1007/BF00473076

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  • DOI: https://doi.org/10.1007/BF00473076

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