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

Kanakam, Charles C. ; Mani, Neelakandha S. ; Ramanathan, Halasya ; Subba Rao, G. S. R. (1989) Syntheses based on cyclohexadienes. Part 2. Convenient synthesis of 6-alkylsalicylates, 6-alkyl-2,4-dihydroxybenzoate, and 2,5-dialkylresorcinols Journal of the Chemical Society, Perkin Transactions 1 (11). pp. 1907-1913. ISSN 1472-7781

Full text not available from this repository.

Official URL: http://pubs.rsc.org/en/content/articlelanding/1989...

Related URL: http://dx.doi.org/10.1039/P19890001907

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 regiospecific 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-methoxymellein (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:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:55734
Deposited On:19 Aug 2011 03:24
Last Modified:19 Aug 2011 03:24

Repository Staff Only: item control page