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Unusual aluminum chloride-assisted conversion of isopropenyl acetate into 3-acetyl- and 3,5-diacetyl-2,6-dimethyl- 4H-pyran-4-ones

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Abstract

Reflux of isopropenyl acetate with an excess of AlCl3 in 1,2-dichloroethane affords 3,5-diacetyl-2,6-dimethyl-4H-pyran-4-one in 17% yield. The mild acidic cleavage of the latter (2% HCl, 20 °C, 16 h) gives 3-acetyl-2,6-dimethyl-4H-pyran-4-one in 87% yield, whereas this reaction under more drastic conditions (17% HCl, reflux, 3 h) gives 2,6-dimethyl-4H-pyran-4-one in 61% yield.

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Authors and Affiliations

  1. Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, 159 prosp. 100 Let Vladivostoku, 690022, Vladivostok, Russian Federation

    V. L. Novikov, O. P. Shestak & V. A. Denisenko

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  1. V. L. Novikov
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  2. O. P. Shestak
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  3. V. A. Denisenko
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1560–1564, August, 2010.

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Novikov, V.L., Shestak, O.P. & Denisenko, V.A. Unusual aluminum chloride-assisted conversion of isopropenyl acetate into 3-acetyl- and 3,5-diacetyl-2,6-dimethyl- 4H-pyran-4-ones. Russ Chem Bull 59, 1600–1604 (2010). https://doi.org/10.1007/s11172-010-0283-0

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  • DOI: https://doi.org/10.1007/s11172-010-0283-0

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