Benzyl Bromide → ethyl-3,4-dibenzyloxybenzoate

Participants

Reaction Steps

Ethyl-3,4-dihydroxy benzoate, 4 (27.3 g, 150 mmol), benzyl bromide (40.4 mL, 340 mmol) and potassium carbonate (41.4 g, 300 mmol) in acetone (350 mL) were reacted in a similar manner as described for 8 to afford 9. Yield 41.4 g (76%); mp 68-69° C.; MS (FAB) 363 (M++1); IR (KBr) 1889, 1707; 1H NMR (200 MHz, CDCl3) δ 7.65 (s, 1H), 7.63 (dd, J=8.7 Hz, 1.7 Hz, 1H), 7.48-7.25 (m, 10H), 6.91 (d, J=8.3 Hz, 1H), 5.19 (s, 2H), 5.18 (s, 2H), 4.31 (q, J=7.1 Hz, 2H), 1.35 (t, J=7.1 Hz, 3H).

Provenance & Evidence