2,2-Diethylpropanedioate → 4-Acetyl-3,5-dimethoxybenzoic acid

Participants

Reaction Steps

3,5-Dimethoxy-4-ethyl-benzoyl chloride. Starting from 4-carbomethoxy-2,6-dimethoxy-benzoyl chloride and diethyl-malonate, and following the procedure described by H. G. Walker et al., in Journal Am.Chem.Soc., 68, 1387 (1946), the methyl ester of 4-acetyl-3,5-dimethoxy-benzoic acid is obtained, m.p. 100°-102°C. This compound is hydrolized under alkaline conditions to the corresponding acid. (M.p. 174°-179°C from ethanol/water). The conversion of the -COCH3 group at the position 4 to --CH2CH3 is achieved by the reductive method described by Huang Minlon in Journal Am.Chem.Soc., 68, 2487, 1946. The obtained 3,5-dimethoxy-4-ethylbenzoic acid has m.p. 190°-91°C (from methanol/water). The corresponding chloride is obtained in the same way as for the compound under A). M.p. 88°-89°C (from diethyl ether).

Provenance & Evidence