3-Chloro-4'-methoxypropiophenone → 4-Acryloylphenol

Participants

Reaction Steps

2-Chloroethyl 4-methoxyphenyl ketone (b) (69.4 g) was dissolved in methylene chloride (200 mL), to which was added aluminium chloride (130.8 g) little by little. The resulting mixture was heated with a mantle heater for 2 hours under reflux. After the reaction, the reaction liquid was cooled and poured into ice, and the organic phase was extracted out with ethyl acetate (200 mL) and transferred into a separating funnel. The organic phase was washed with water, and then processed with aqueous 2 M NaOH solution to extract out the intended product into the solution. The aqueous alkali solution was acidified with 6 M hydrochloric acid, and then again extracted with ethyl acetate. The solvent was evaporated away under reduced pressure, and the residue was recrystallized from toluene to obtain 37.9 g of colorless crystals, 4-hydroxyphenyl vinyl ketone (c).

Provenance & Evidence