The stobbe condensation of anisaldehyde and dimethyl succinate: synthesis of the lactone of 2-carboxy-4-hydroxy-6-methoxytetralone-1

Banerjee, D. K. ; Bagavant, G. (1959) The stobbe condensation of anisaldehyde and dimethyl succinate: synthesis of the lactone of 2-carboxy-4-hydroxy-6-methoxytetralone-1 Proceedings of the Indian Academy of Sciences, Section A, 50 (4). pp. 282-288. ISSN 0370-0089

[img]
Preview
PDF - Publisher Version
1MB

Official URL: http://www.ias.ac.in/j_archive/proca/50/4/282-288/...

Related URL: http://dx.doi.org/10.1007/BF03048864

Abstract

Condensation of anisaldehyde and dimethyl succinate in presence of potassium tert.-butoxide yielded methyl hydrogen p-methoxyphenylitaconate. Reduction followed by cyclisation with polyphosphoric acid furnished 3-methoxycarbonyl-7-methoxytetralone-1 and 3-carboxy-7-methoxytetralone-1. The lactone of 1-hydroxy-3-carboxy-7-methoxy-tetralin was obtained as a product in the aluminium isopropoxide reduction of 3-methoxy-carbonyl-7-methoxytetralone-1; or by reducing the sodium salt of 3-carboxy-7-methoxytetralone-1 with sodium borohydride followed by lactonisation with dilute sulphuric acid. Oxidation of this lactone yielded the lactone of 2-carboxy-4-hydroxy-6-methoxytetralone-1.

Item Type:Article
Source:Copyright of this article belongs to Indian Academy of Sciences.
ID Code:26369
Deposited On:06 Dec 2010 12:39
Last Modified:17 May 2016 09:40

Repository Staff Only: item control page