Phosgene → 2-(Chloromethyl)benzoyl chloride

Participants

Reaction Steps

2 mol of phthalide (268 g) were initially charged with 27.8 g of TPPO (0.1 mol) and 7.9 g (0.04 mol) of BF3 etherate. At 140-150° C., a total of 233 g of gaseous phosgene (2.33 mol) were introduced over a period of 8 h. After an extra stirring time of 1 h at 140° C., the excess phosgene was stripped using nitrogen. The discharge (415 g) contained 88.4 GC area % of o-chloro-methylbenzoyl chloride and 0.1% of phthalide. Fractional distillation of the crude discharge gave 363 g (96% of theory) of o-chloromethylbenzoyl chloride of a purity of 99.8%.

Provenance & Evidence