1,3-Dibromopropane → 1-[4-(3-Bromopropoxy)-3-methylphenyl]ethanone

Participants

Reaction Steps

A mixture of 4-hydroxy-3-methylacetophenone (14.5 g, 96 mmoles), K2CO3 (17.5 g, 144 mmoles), and 1,3- dibromopropane (30 g, 144 mmoles) in acetonitrile (400 ml) was heated at reflux for 6 hours. At the end of the reaction, the solvent was removed on a rotary evaporator, and the crude solid was extracted into dichloromethane (750 ml). The inoluble inorganics were filtered off. The dichloromethane solution was concentrated again to a crude oil (34.5 g). Purification was effected by flash chromatography over a silica gel column (SiO2, 150 g; eluted with 7:3 hexane:dichloromethane, 2 l; and dichloromethane 2 l). The material thus purified weight 14.6 g (56%) and was recrystallized from ethanol. Recrystallization again from ethanol gave analytically pure 1-[4-(3-bromopropoxy)-3- methylphenyl]ethanone, m.p.=59°-61° C.

Provenance & Evidence