4'-Hydroxyacetophenone → 1-(4-(2-Bromoethoxy)phenyl)ethanone

Participants

Reaction Steps

A mixture of 4-hydroxyacetophenone (20 g, 147 mmol) and potassium carbonate (81 g, 588 mmol) was placed into 2 L round bottomed flask and acetone (1 L) was added. To this reaction mixture dibromoethane (38 mL) was added in one portion, and then the reaction mixture was allowed to reflux for 36 hours, under nitrogen atmosphere. The reaction mixture was cooled to room temp, and filtered off, residue was washed with acetone (2×100 mL), and the filtrates were combined and concentrated under reduced pressure. The crude was chromatographed over silica gel by using 10-15% ethyl acetate/pet. ether (2 L), affording the title compound 7 g (20%) as a white solid. Mp. 58-61° C.

Provenance & Evidence