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Preparation of α -methyl- γ -butyrolactone: Mechanism of its formation and utilization in 2-methyl-1-tetralone synthesis
Semak, Vladislav, Boháč, Andrej, Sališová, Marta, Addová, Gabriela and Danko, Peter Preparation of α -methyl- γ -butyrolactone: Mechanism of its formation and utilization in 2-methyl-1-tetralone synthesis Chemical Papers, Vol.62, No. 3, 2008, 275-280
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Document type:
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Článok z časopisu / Journal Article |
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Collection:
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Chemical papers
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| Author(s) |
Semak, Vladislav
Boháč, Andrej
Sališová, Marta
Addová, Gabriela
Danko, Peter
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| Title |
Preparation of α -methyl- γ -butyrolactone: Mechanism of its formation and utilization in 2-methyl-1-tetralone synthesis
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| Journal name |
Chemical Papers
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| Publication date |
2008
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| Year available |
2008
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| Volume number |
62
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| Issue number |
3
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| ISSN |
0366-6352
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| Start page |
275
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| End page |
280
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| Place of publication |
Poland
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| Publisher |
Versita
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| Collection year |
2008
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| Language |
english
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| Subject |
250000 Chemical Sciences
250300 Organic Chemistry
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| Abstract/Summary |
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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