Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Studies on the Condensation of Phenols with Unsaturated Dibasic Acids. II
Condensation of m-Cresol with Fumaric Acid, Maleic Acid and Malic Acids.
Takeshi YOSHINOIchiro KIJIMAMichio SUGIURARyosuke FURUYA
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1963 Volume 21 Issue 5 Pages 373-376

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Abstract
Detailed investigation on the synthesis of 7-methylcoumarin by condensation of m-cresol and fumaric acid, maleic acid or malic acid in the presence of sulfuric acid has been carried out, and the reaction mechanism wass discussed 7-methylcoumarin was obtained in slightly above 20% yield . In the case of malic acid was given the highest yield. The mechanism of reaction is the same as in the case of 6-methylcoumarin. Accordingly the first step is esterification, sulfuric acid being esterifying agent, and the second step is the formation of 7-methylcoumarin, sulfuric acid acting as a cyclization agent. It is considered the-Pechamann reaction have taken place in the case of malic acid.
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© The Society of Syhthetic Organic Chemistry, Japan
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