Preparation of α-methyl-γ-butyrolactone: Mechanism of its formation and utilization in 2-methyl-1-tetralone synthesis-Reference-Cited by-同舟云学术

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

Published:2008-01-01 Issue:3 Volume:62 Page:
ISSN:1336-9075
Container-title:Chemical Papers
language:
Short-container-title:

Author:

Semak Vladislav,Boháč Andrej,Sališová Marta,Addová Gabriela,Danko Peter

Abstract

Abstractα-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.

Publisher

Springer Science and Business Media LLC

Subject

Materials Chemistry,Industrial and Manufacturing Engineering,General Chemical Engineering,Biochemistry,General Chemistry

Reference15 articles.

1. Selective mono - methylation of arylacetonitriles and methyl arylacetates by dimethyl carbonate of Chemical Perkin Transactions;Selva;Journal Society,1994

2. Ortho effect in the Bergman cyclization : Interception of p - benzyne intermediate by intramolecular hydrogen abstraction of Organic;Zeidan;Journal Chemistry,2006

3. Why is alkylation of an enolate accompanied by so much polyalkylation;Streitwieser;Organic Letters,2001

4. New reactions of potassium naphthalenide with β - , γ - and δ - lactones : an efficient route to α - alkyl γ - and δ - lactones and α , β - unsaturated carboxylic acid esters of Organic;Kowalczuk;Journal Chemistry,1992

5. The effects of cyclic terminal groups in di - and tri - arylmethane dyes Part Steric and electronic effects in derivatives of Victoria Blue of Chemical Perkin Transactions;Guinot;Journal Society,1998

Cited by 3 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Upgrading of Biobased Lactones with Dialkylcarbonates;ACS Sustainable Chemistry & Engineering;2014-07-29

2. 1 H NMR spectra. Part 29§: proton chemical shifts and couplings in esters-the conformational analysis of methyl γ-butyrolactones;Magnetic Resonance in Chemistry;2012-11-05

3. Efficient synthesis of 2-alkyl-2-hydroxy-6-X-1-tetralones;Arkivoc;2008-06-28