ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

Syntheses based on cyclohexadienes. Part 2. Convenient synthesis of 6-alkylsalicylates, 6-alkyl 2,4-dihydroxybenzoate, and 2,5-dialkylresorcinols

Charles, Kanakam C and Neelakandha, Mani S and Halasya, Ramanathan and Subba, Rao GSR (1989) Syntheses based on cyclohexadienes. Part 2. Convenient synthesis of 6-alkylsalicylates, 6-alkyl 2,4-dihydroxybenzoate, and 2,5-dialkylresorcinols. In: Journal of the Chemical Society, Perkin Transactions 1 (11). pp. 1907-1913.

[img] PDF
syn.pdf - Published Version
Restricted to Registered users only

Download (1003Kb) | Request a copy
Official URL: http://www.rsc.org/publishing/journals/P1/article....

Abstract

A one pot synthesis of 6-alkylsalicylates and 6-alkyl-2,4- dihydroxybenzoates is described. Cycloaddition of 1-methoxycyclohexa-1,4- or 1,3-dienes with alkylpropiolic esters results in the regio-specific formation of 2-alkyl-6-methoxybenzoates. Thus, methyl 2-methoxy-6-methyl benzoate, methyl 2,4-dimethoxy-6-methylbenzoate, methyl 2,5-dimethoxy-6-methylbenzoate, methyl 2-methoxy-4,6-dimethylbenzoate, and ethyl 2-butyl-4,6-dimethoxybenzoate, have been prepared. By making use of this method, the synthesis of two dihydroisocoumarins namely (±)-mellein (12) and (±)-6-methoxy- mellein (14) is described. Employing a similar strategy, a novel route to 2,5-dialkylresorcinols has been developed. Stemphol (24b) and the antibiotic DB2073 (24d) have been synthesized.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 20 Jul 2010 09:36
Last Modified: 19 Sep 2010 06:11
URI: http://eprints.iisc.ernet.in/id/eprint/30369

Actions (login required)

View Item View Item