4'-Hydroxyacetophenone → 1-[4-(2-Chloroethoxy)phenyl]ethanone

Participants

Reaction Steps

To a solution of 4′-hydroxyacetophenone (101 g, 0.74 mole) in acetone (800 mL) was added 1-bromo-2-chloroethane (638 g, 4.45 mole) followed by K2CO3 (307 g, 2.22 mole). The reaction was heated to reflux for 48 h then filtered. The K2CO3 was washed with acetone (1 L) and the filtrate was evaporated. The residue was then partitioned between EtOAc (800 mL) and 1 N NaOH (250 mL). The organic layer was washed with 1 N NaOH (250 mL) then dried and evaporated to yield 146 g of the desired product (99% yield).

Provenance & Evidence