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Synthesis of 4,6-(and 5,7-)dimethoxy-3,3-dimethyl-1-indanones

Kasturi, TR and Abraham, EM and Prasad, RS (1974) Synthesis of 4,6-(and 5,7-)dimethoxy-3,3-dimethyl-1-indanones. In: Tetrahedron, 30 (16). pp. 2887-2890.

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Official URL: http://dx.doi.org/10.1016/S0040-4020(01)97460-5


Grignard reaction of ethyl 3-(3,5-dimethoxyphenyl)-propionate (4) followed by cyclodehydration of the carbinol (5) with conc H2SO4 gave 4,6-dimethoxy-3,3-dimethylindane (6). Oxidation of the indane (6) with CrO3-pyridine complex in methylene chloride gave 4,6-dimethoxy-3,3-dimethylindan-1- one (1) in high yield. Conjugate addition of methyl magnesium iodide to methyl α-cyano-β-methyl-3,5-dimethoxycinnamate (11), prepared from 3,5-dimethoxyacetophenone (10) by Knoevenagel condensation, resulted in methyl 2-cyano-3-(3,5-dimethoxyphenyl)-3,3-dimethylpropionate (12). Refluxing the ester (12) with aq DMSO containing sodium chloride gave the corresponding nitrile (15) which underwent Höesch reaction to yield 5,7-dimethoxy-3,3-dimethylindan-1-one (2).

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 01 Jan 2010 10:01
Last Modified: 22 Feb 2012 10:19
URI: http://eprints.iisc.ac.in/id/eprint/23191

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