1-Bromo-3-chloropropane → 4-(3-Chloropropoxy)benzamide

Participants

Reaction Steps

A mixture of 50 g (0.365 mole) of 4-hydroxybenzamide, 114.8 g (0.729 mole) of 1-bromo-3-chloropropane and 151.3 g (1.1 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 20 hr. The mixture was concentrated under reduced pressure and the rsidue was stirred with 1.2 liter of water to remove inorganic solids. The mixture was filtered and the filter cake was washed with water and petroleum ether and dried to yield 75.5 g (97%) of the title compound as a white solid. An analytical sample was recrystallized from ethyl acetate, m.p. 142°-143° C.

Provenance & Evidence