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

Participants

Reaction Steps

To a solution of ethyl-3,5-dihydroxy benzoate, 3 (16.8 g, 92 mmol) in acetone (350 mL) were added potassium carbonate (27.6 g, 200 mmol) and benzyl bromide (23.8 mL, 200 mmol) and stirred at room temperature for 9 h. Reaction mixture was filtered, concentrated on rotavapor and the crude product purified by column chromatography to afford 8. Yield 24.7 g (74%); mp 63-65° C.; MS (FAB) 363 (M++1); IR (KBr) 1824, 1708; 1H NMR (200 MHz, CDCl3) δ 7.34-7.35 (m, 10H), 7.30 (d, J=2.3 Hz, 2H), 6.79 (t, J=2.2 Hz, 1H), 5.07 (s, 4H), 4.36 (q, J=7.1 Hz, 2H), 1.38 (t, J=7.1 Hz, 3H).

Provenance & Evidence