Myristyl bromide → 3,4-Bis(tetradecyloxy)benzoic acid methyl ester

Participants

Reaction Steps

A mixture of 1.0 g (6.6 mmol) of 3,4-dihydroxybenzoic acid methyl ester, 4.1 ml (14 mmol) of 1-bromotetradecane and 2.5 g (17.9 mmol) of potassium carbonate in 50 ml of DMF was stirred and heated at 100° for 65 hours. The solvent was removed using high vacuum, water was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was recrystallized from methanol-water to give 1.1 g (30% yield, mp 49°-50°) of 3,4-bis(tetradecyloxy)benzoic acid methyl ester.

Provenance & Evidence