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Russian Chemical Bulletin

, Volume 59, Issue 8, pp 1600–1604 | Cite as

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

  • V. L. Novikov
  • O. P. Shestak
  • V. A. Denisenko
Full Articles

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.

Key words isopropenyl acetate aluminum chloride acetylacetone α-pyrones heterocyclization. 

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Copyright information

© Springer Science+Business Media, Inc.  2010

Authors and Affiliations

  • V. L. Novikov
    • 1
  • O. P. Shestak
    • 1
  • V. A. Denisenko
    • 1
  1. 1.Pacific Institute of Bioorganic ChemistryFar-Eastern Branch of the Russian Academy of SciencesVladivostokRussian Federation

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