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Chemical Papers

, Volume 62, Issue 3, pp 275–280 | Cite as

Preparation of α-methyl-γ-butyrolactone: Mechanism of its formation and utilization in 2-methyl-1-tetralone synthesis

  • Vladislav Semak
  • Andrej BoháčEmail author
  • Marta Sališová
  • Gabriela Addová
  • Peter Danko
Original Paper

Abstract

α-Methyl-γ-butyrolactone (III) has been prepared directly from γ-butyrolactone (I) in 89 % yield by selective monomethylation conditions: K2CO3/DMC/210°C/7 h. The reaction mechanism was elucidated and described. An intermediate and two byproducts: methyl tetrahydro-3-methyl-2-oxofuran-3-carboxylate (II), 3-(methoxycarbonyl)propyl methyl carbonate (IV) and 3-(methoxycarbonyl)butyl methyl carbonate (V) were identified. The high temperature disproportionation of K2CO3 in the presence of dimethyl carbonate to MeOK was observed. The new selective synthesis of 2-methyl-1-tetralone (VI) from α-methyl-γ-butyrolactone (III) by Friedel-Crafts conditions was performed in 79 % yield.

Keywords

dihydro-3-methylfuran-2(3H)-one α-methyl-γ-butyrolactone dimethyl carbonate reaction mechanism selective monomethylation 2-methyl-1-tetralone annulation 

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Copyright information

© Versita 2008

Authors and Affiliations

  • Vladislav Semak
    • 1
  • Andrej Boháč
    • 1
    Email author
  • Marta Sališová
    • 1
  • Gabriela Addová
    • 2
  • Peter Danko
    • 3
  1. 1.Department of Organic ChemistryComenius UniversityBratislavaSlovakia
  2. 2.Chemical Institute, Faculty of Natural SciencesComenius UniversityBratislavaSlovakia
  3. 3.Synkola Ltd.BratislavaSlovakia

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