Benzyl Chloride → HCID 12398517, compound

Participants

Reaction Conditions

Reaction Steps

K2CO3 (66.8 g, 0.48 mol) was added to a stirred solution of ethyl 3-hydroxybenzoate (1) (40.0 g, 0.24 mol) and (chloromethyl)benzene (33.5 g, 0.26 mol) in DMF (256 mL) and the reaction mixture was heated at 90° C. for 3 h. The reaction mixture was filtered through Celite, the filtrate was diluted with water (500 mL), extracted with EtOAc (500 mL). The organic layer was washed with brine (500 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give ethyl 3-(benzyloxy)benzoate (2) as colorless liquid. Yield (61.0 g, 98%); 1H NMR (400 MHz, DMSO-d6) δ 7.56-7.53 (m, 2H), 7.47-7.44 (m, 3H), 7.39 (t, J=7.2 Hz, 2H), 7.35-7.29 (m, 2H), 5.17 (s, 2H), 4.30 (q, J=7.2 Hz, 2H), 1.31 (t, J=7.2 Hz, 3H).

Provenance & Evidence