Potassium Carbonate → HCID 54194410, compound

Participants

Reaction Steps

A mixture of 2.0 g (11.9 mmol) of 3,5-dihydroxybenzoic acid methyl ester, 3.8 g (11.9 mmol) of 3-[(4-phenylmethoxy)phenoxy]propyl bromide and 1.7 g (12.3 mmol) of potassium carbonate in 40 ml of acetone and 2 ml of DMF was stirred at reflux for 24 hours. The solvents were removed at reduced pressure, the residue was stirred with methylene chloride and filtered. The filtrate was concentrated to a solid which was recrystallized from methylene chloride-methanol to give 1.77 g, mp 134°-136°, of 3,5-bis[3-[4-(phenylmethoxy)phenoxy]propoxy]benzoic acid methyl ester. The filtrate was concentrated to a solid which was purified by chromatography on 20 g of silica gel (230-400 mesh) using 10% ethyl acetate-hexane to give 1.47 g (30% yield, mp 120°-122°) of 3-hydroxy-5-[3-[4-(phenylmethoxy)phenoxy]propoxy]benzoic acid methyl ester.

Provenance & Evidence