4-Chlorophenol → 3-(4-Chlorophenoxy)2-methyl-1-propene

Participants

Reaction Steps

A mixture of 4chlorophenol (10 g, 0.78 mol) and sodium hydride (1.9 g, 0.08 mol) is heated to reflux for 30 min in 30 ml of THF and then cooled. 3-Chloro-2-methyl-1-propene (7.3 g, 0.08 mol) in 10 ml THF is added and the mixture is heated to reflux. After 24 hr, an additional equivalent of 3-chloro-2-methyl-1-propene is added and the mixture heated under reflux for another 24 hr. The reaction mixture is cooled and diluted with ether to 150 ml, washed with 20% NaOH (2X) and with water until neutral, then dried and solvent is removed to yield 3-(4-chloro-phenoxy)-2-methyl-1-propene.

Provenance & Evidence