Phenol → HCID 21957453, compound

Participants

Reaction Steps

Cesium carbonate (226 mg, 0.69 mmol, 1.5 eq) was added to a stirred solution of 3-[[(methylsulfonyl)oxy]methyl]-4-(2-phenylethoxy)benzaldehyde (155 mg, 0.46 mmol, 1 eq) and phenol (175 mg, 1.86 mmol, 4 eq). The reaction mixture was stirred for 48 h, then partitioned between diethyl ether (50 mL) and water (50 mL). The two layers were separated and the organic layer washed with water (2×100 mL), 1M sodium hydroxide (100 mL), brine (100 mL) and then dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel. Elution with dichloromethane gave a gummy solid, which when triturated with ether crystallized to a white powder (105 mg, 68%). RF (petroleum ether:diethyl ether, 1:1) 0.40. 1H NMR (CDCl3) δ 9.90 (s, 1H, O═C—H), 8.04 (s, 1H, ArH), 7.84 (d, 1H, J 8.4 Hz, ArH), 5.08 (s, 2H, CH2OPh), 4.34 (t, 2H, J 6.5 Hz, OCH2CH2Ph), 3.16 (t, 2H, J 6.5 Hz, OCH2CH2Ph).

Provenance & Evidence