Phenol, tribromo- → o-Chloromethylbenzoic acid tribromophenyl ester

Participants

Reaction Conditions

Reaction Steps

In a two-liter three-necked flask, 40 g of sodium hydroxide was dissolved in 950 ml of methyl glycol at 60° C, and then 331 g (= 1 mole) of tribromophenol was stirred in, and then 189 g (= 1 mole) of o-chloromethyl benzoyl chloride was added, drop by drop, with stirring, over a period of 13/4 hours, at a reaction mixture temperature not exceeding 40° C, into the clear phenolate solution, cooled to 30° to 40° C. Stirring was then continued for one hour at room temperature; the mixture was then cooled to 0° C, the crystallizate was suction filtered and washed free of sodium chloride with water, and dried at 80° C in a vacuum drying chamber. 397 g (= 82% yield) was obtained of o-chloromethylbenzoic acid tribromophenyl ester melting at 180°-110° C.

Provenance & Evidence