Reaction of phenols with cyclic α, β-unsaturated acids: an efficient one-pot synthesis of hexahydroxanthones

Merchant, Jayasukhlal R. ; Fernandes, Neville V. ; Waghulde, Vidyullata C. (1996) Reaction of phenols with cyclic α, β-unsaturated acids: an efficient one-pot synthesis of hexahydroxanthones Proceedings of the Indian Academy of Sciences - Chemical Sciences, 108 (2). pp. 379-398. ISSN 0253-4134

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Official URL: http://www.ias.ac.in/j_archive/chemsci/108/vol108c...

Related URL: http://dx.doi.org/10.1007/BF02871248

Abstract

A number of 1,2,3,4,4a,9a-hexahydro-9H-xanthen-9-ones have been prepared by the reaction of various phenols with 1-cyclohexene-1-carboxylic acids in the presence of polyphosphoric acid (PPA). However the reaction of 2,3-dimethylphenol gave in addition two isomeric 6,7-dimethyl-dodecahydro-indeno (1,2-a)xanthen-8,13-diones. 2,5-Dimethylphenol reacted differently giving the hexahydro-9H-fluoren-9-one instead. Dehydrogenation of the hexahydroxanthones with Pd/C in refluxing diphenyl ether afforded the corresponding xanthones in good yields (80-95%).

Item Type:Article
Source:Copyright of this article belongs to Indian Academy of Sciences.
Keywords:Phenols; 1-cyclohexene-1-carboxylic Acid; Polyphosphoric Acid; 1,2,3,4,4a,9a-hexahydro-9H-xanthen-9-ones; 6,7-dimethyl-dodecahydro-indeno (1,2-a)xanthen-8,13-dione; Hexahydro-9H-fluoren-9-one
ID Code:31718
Deposited On:30 Mar 2011 12:14
Last Modified:03 Apr 2012 11:44

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