4'-Hydroxyacetophenone → 1-[4-(3-Chloropropoxy)phenyl]ethanone

Participants

Reaction Steps

A mixture of p-hydroxyacetophenone (106 g) and 1-bromo-3-chloropropane (309 mL) in methanol (800 mL) was treated with potassium hydroxide (65.5 g). The mixture was stirred at reflux temperature for 2 hours when an additional portion of potassium hydroxide (65.5 g) was added and the resulting mixture maintained at reflux temperature for 16 hours. The reaction was cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo and unreacted 1-bromo-3-chloropropane removed ia distillation. The residue was dissolved in ether (500 mL), washed with water (500 mL), dried over magnesium sulfate, filtered and evaporated to yield the title compound (147 g).

Provenance & Evidence