Benzyl Bromide → Methyl 3,5-bis(benzyloxy)benzoate

Participants

Reaction Steps

A mixture of 25.0 g (0.15 mol) of 3,5-dihydroxybenzoic acid methyl ester, 44 ml (0.37 mol) of benzyl bromide and 82 g (0.60 mol) of potassium carbonate in 300 ml of DMF was stirred and heated at 85° under argon for 45 hours. The cooled reaction mixture was filtered and the filtrate was concentrated at reduced pressure. The residue was treated with methylene chloride and the extract was filtered again to remove salts. Crystallization from methylene chloride-methanol gave 41.9 g (81% yield, mp 64°-66°) of 3,5-bis(phenylmethoxy)benzoic acid methyl ester.

Provenance & Evidence