1,2-Dimethoxyethane → HCID 21997568, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-methoxycarbonylphenylboronic acid (2.01 g) and 1-bromo-4-ethoxymethylbenzene (2.00 g) in a mixed solvent of ethylene glycol dimethyl ether (20 ml) and 2M aqueous sodium carbonate solution (6 ml) was added tetrakis(triphenylphosphine)palladium (0) (0.54 g). The mixture was heated at 80° C. for 5 hours. After cooling to room temperature, water (150 ml) was added to the reaction mixture and the resulting precipitate was collected by filtration, washed thoroughly with water and dried to give a crude solid. This solid was purified by column chromatography on silica gel (60 g) eluting successively with the following solvents: (1) n-hexane:ethyl acetate=50:1, (2) n-hexane:ethyl acetate=10:1. The fractions containing the object compound were concentrated and dried to give methyl 4-(4′-ethoxymethylphenyl)benzoate as a white solid (1.85 g).

Provenance & Evidence