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

Participants

Reaction Steps

A mixture of 4-chlorophenol (10 g, 0.078 mol) and potassium carbonate (32.25 g, 0.233 mol) in 20 ml DMF is stirred for 30 min at 25°. 1.1 Equivalents of 3-chloro-2-methyl-1-propene in 10 ml DMF is added dropwise at 0° and the mixture is allowed to warm to RT. After stirring at RT for 19 hr, the reaction is checked by thin layer chromatography (TLC) developing with 30% ethyl acetate/hexane. As some starting alcohol is still present, another 0.5 equivalent of 3-chloro-2-methyl-1-propene is added (a total of 1.6 equivalents) and the reaction mixture is heated at 50° for 7 hr. The reaction product is worked up with ice water and ether. The organic phase is washed with 5% NaOH, water until neutral, brine, and dried over magnesium sulfate and solvent is removed to give 3-(4-chlorophenoxy)-2-methyl-1-propene.

Provenance & Evidence