4-Hydroxybenzyl Alcohol → HCID 18621258, compound

Participants

Reaction Steps

A solution of 4-(hydroxymethyl)phenol (38.0 g, 0.31 mmol) and 2,6-dichlorobenzyl bromide (73.4 g, 0.31 mmol) in DMF (500 ml) was treated with caesium carbonate (100 g, 0.31 mmol) and heated to 60° for 16 h. The mixture was cooled to room temperature and the solvent evaporated in vacuo. The residue was partitioned between EtOAc (250 ml) and water (250 ml), the aqueous layer was separated and extracted with EtOAc (250 ml) and the combined organic layers washed with 10% hydrochloric acid (100 ml), NaHCO3 solution (100 ml) and brine (200 ml), dried (MgSO4) and the solvent evaporated in vacuo to give the title compound as a brown oil (88.4 g) which was used without further purification. δH (CDCl3) 7.38-7.21 (5H, m, ArH), 7.02 (2H, d, J 8.7 Hz, ArH), 5.28 (2H, s, CH2OAr) and 4.63 (2H, s, CH2OH).

Provenance & Evidence