Phenol → 5-Ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

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Reaction Steps

5-Ethoxy-1-tetralone was prepared from the commercially available 5-methoxy-1-tetralone by treatment with AlCl3 in benzene followed by alkylation of the resulting phenol with ethyl iodide in acetone in the presence of potassium carbonate. The resulting tetralone was then treated by the procedures described in International Patent Application Number WO 89/06645 for the preparation of 5-methoxy 1,2,3,4-tetrahydronaphthalene-1-carboxylic acid to yield 5-ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid. The title compound was prepared from 5-ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid by the procedures described in Example 10 through 15 to yield the product as a white solid. m.p. 219°-221° C. 1H NMR (DMSO-b6, 300 MHz) δ1.32 (t, 3H), 1.65-1.9 (m, 4H), 2.4-2.7 (m, 2H), 2.59 (s, 3H), 3.0-3.3 (m, 3H), 4.0 (m, 2H), 6.78 (d, 1H), 6.84 (d, 1H), 7.12 (t, 1H), 8.6 (bs, 2H).

Provenance & Evidence