反应详情

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.

1. temperatureThe resulting solution was refluxed for 5 h
2. customthe solvent evaporated under reduced pressure
3. customThe residue was partitioned between ether and water
4. washThe ether layer was washed with 10% aqueous NaOH solution and brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue was recrystallized from absolute ethanol affording 7.6 g (91.7%) of methyl 5-chloro-2-phenylmethoxybenzoate as white crystals