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

Kasturi, T. R. ; Abraham, E. M. ; Prasad, R. S. (1974) Synthesis of 4,6-(and 5,7-) dimethoxy-3,3-dimethyl-1-indanones Tetrahedron, 30 (16). pp. 2887-2890. ISSN 0040-4020

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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 Hoesch reaction to yield 5,7-dimethoxy-3,3-dimethylindan-1-one (2).

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