3-Iodophenol → Methyl alpha-(3-iodophenoxy)crotonate

Participants

Reaction Steps

A solution of 11 g (0.05 mol) of 3-iodophenol is added dropwise at 0 to 5° C. to a solution of 3 g (0.055 mol) of KOH in 30 ml of dimethylformamide. 9 g (0.05 mol) of methyl 3-bromocrotonate are added at this temperature, and stirring of the solution is continued for one hour at room temperature. The mixture is treated with ice-water and extracted using methyl tert-butyl ether, and the methyl tert-butyl ether phase is dried over Na2SO4 and concentrated in vacuo. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate: 99/1). This gives 9.7 g (61% of theory) of the title compound as an oil.

Provenance & Evidence