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

✍ Scribed by Vladislav Semak; Andrej Boháč; Marta Sališová; Gabriela Addová; Peter Danko

Book ID: 111491137
Publisher: Versita
Year: 2008
Tongue: English
Weight: 190 KB
Volume: 62
Category: Article
ISSN: 0366-6352
DOI: 10.2478/s11696-008-0023-1

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✦ Synopsis

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.

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