2,4-Dichlorobenzaldehyde → 1-(2,4-Dichlorophenyl)prop-2-en-1-ol

Participants

Reaction Steps

A solution of 20.0 g (114 mmol) of 2,4-dichlorobenzaldehyde in 200 ml of diethyl ether was slowly added dropwise to 137 ml (137 mmol) of a 1N solution of vinylmagnesium bromide in tetrahydrofuran at RT under argon. After heating under reflux for 1 h, the reaction mixture was added to saturated aqueous ammonium chloride solution and diluted with diethyl ether and water. The phases were separated, and the organic phase was washed twice with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5/1) to result in 18.8 g (81% of theory) of the title compound.

Provenance & Evidence