2-Chloroethanol → (4-(2-Hydroxyethoxy)phenyl)(4-hydroxyphenyl)methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 4,4′-dihydroxybenzophenone (3.0 g, 13.9 mmol) in DMF (30 mL) was added Cs2CO3 (13.55 g, 41.6 mmol). The mixture was heated at 80° C. under nitrogen for 1 h. Cooled to room temperature, NaI (2.08 g, 13.9 mmol) was added, followed by dropwise addition of a solution of 2-chloroethanol (1.03 mL, 15.3 mmol) in DMF (7 mL) with stirring. The reaction mixture was heated at 80° C. under nitrogen overnight. The mixture was cooled to room temperature and quenched with saturated aqueous NH4Cl (100 mL), then extracted with EtOAc (3×60 mL). The organic layers were combined and washed with water, brine and dried over Na2SO4. Concentration gave a reddish brown oil which was further purified by chromatography on a silica gel column eluted with a gradient from hexanes to 80% EtOAc:hexanes yielded a pale white solid. Trituration with 10% EtOAc:hexanes afforded 1.30 g (36%) of 96 as a white solid. mp 146-147° C. 1H NMR (400 MHz, CD3OD): δ 3.85-3.95 (m, 2H), 4.10-4.20 (m, 2H), 6.87 (d, J=8.8 Hz, 2H), 7.06 (d, J=8.7 Hz, 2H), 7.67 (d, J=8.6 Hz, 2H), 7.73 (d, J=8.8 Hz, 2H). LRMS (ESI): m/z 259 (M+H)+, 257 (M−H)−.

Provenance & Evidence