Benzyl Bromide → Methyl 2-(benzyloxy)-5-chlorobenzoate

Participants

Reaction Steps

To a solution of methyl 5-chlorosalicylate (5.58 g, 0.03 mol) in 20 ml of dry acetone were added anhydrous K2CO3 (4.55 g, 0.033 mol) and benzylbromide (5.64 g, 0.033 mol). The resulting solution was refluxed for 5 h and the solvent evaporated under reduced pressure. The residue was partitioned between ether and water. The ether layer was washed with 10% aqueous NaOH solution and brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting residue was recrystallized from absolute ethanol affording 7.6 g (91.7%) of methyl 5-chloro-2-phenylmethoxybenzoate as white crystals: mp 54.5°-55° C.; IR (KBr) 1740 (ester) cm-1 ; NMR (CDCl3, 90 MHz) δ 3.90 (s, 3H, CO2CH3), 5.16 (s, 2H, OCH2Ph), 6.93 (d, 1H, ArH, J=8.9 Hz), 7.20-7.55 (m, 6H, ArH), 7.79 (d, 1H, ArH, J=2.9 Hz). Anal calcd. for (C15H13ClO3): C, 65.11; H, 4.73; Cl, 12.81. Found: C, 65.33; H, 4.88; Cl, 13.08.

Provenance & Evidence