Methanol → Methyl 4-(benzyloxy)benzoate

Participants

Reaction Steps

To a solution of 75 g of methyl 4-hydroxybenzoate in 700 ml THF at 22° C. were added 19.7 g of a 60% dispersion of sodium hydride in mineral oil. After the mixture was stirred for 90 minutes, 84.3 g of benzyl bromide was added dropwise. The reaction was heated at reflux for 18 hours, cooled to room temperature and 50 ml methanol was added. The mixture was evaporated and the resulting residue extracted with three portions of ethyl acetate. The combined organic extracts were washed with water and brine, dried over magnesium sulfate and evaporated to a solid. Recrystallization from cold methanol gave 28.7 g of the title compound: 300 MHz 1H NMR (CDCl3) δ3.96 (s, 3 H), 5.19 (s, 2 H), 7.05 (d, J=9 Hz, 2 H), 7.42 (s, 5 H), 8.05 (d, J=9 Hz, 2 H).

Provenance & Evidence