2-Chloroethyl vinyl ether → 4-[2-(Ethenyloxy)ethoxy]benzoic acid

Participants

Reaction Conditions

Reaction Steps

76.97 g (722 mmol) of a chloroethylvinylether, 9.70 g (30.1 mmol) of a tetrabutylammoniumbromide, and 100.00 g (602 mmol) of ethyl 4-hydroxybenzoate, all manufactured by Tokyo Kasei Kogyo Co., Ltd. were mixed with an N-methylpyrrolidone solvent and stirred at a temperature of 120° C. for 3 hours so as to be reacted. The resulting solution was diluted with water and extracted with ethyl acetate so as to remove the solvent thereby obtaining a crude ethyl 4-(2-vinyloxyethoxy)benzoate. A solution of 43.69 g (662 mmol) of potassium hydroxide with 85% purity was added to the ester and reacted at a temperature of 100° C. for 6 hours to be hydrolyzed, followed by dilution and precipitation with a solution of 91.40 g (662 mmol) of sodium hydrogensulfate monohydrate thereby obtaining a crude crystal of 4-(vinyloxyethoxy)benzoic acid. The resulting crude crystal was dissolved in acetonitrile so as to be recrystallized thereby obtaining a needle-like crystal of 4-(vinyloxyethoxy)benzoic acid with an HPLC purity of 99.5 percent or higher. The yield was 104.0 g (83%).

Provenance & Evidence