p-Pentyloxyphenol → 4-pentoxyphenyl (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}acrylate

Participants

Reaction Steps

23.00 g (97 mmol) 4-pentoxyphenol, 17.6 g (97 mmol) (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}acrylic acid and 1.18 g (9.7 mmol) 4-dimethylaminopyridine were dissolved in 300 ml of dichloromethane. A suspension of 18.6 g (97 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbo-diimide hydrochloride and 200 ml dichloromethane were added dropwise in the course of 40 minutes. After 22 h at room temperature, the reaction mixture was partitioned between dichloromethane and water; the organic phase was washed repeatedly with water, dried over sodium sulphate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 200 g silica gel using cyclohexane:ethyl acetate (7:3) then (1:1) as eluent yielded 36.4 g (94%) 4-pentoxyphenyl (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}acrylate as colourless crystals.

Provenance & Evidence