Carbon Tetrachloride → (1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

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Reaction Steps

N-Bromosuccinimide (19.6 g) and azo(bisisobutyronitrile) (200 mg) were added to a solution of 2,6-dimethylbenzoic acid in carbon tetrachloride (300 ml) and chloroform (50 ml). The mixture was degassed, placed under an atmosphere of argon and then heated under reflux for 2 hours. The mixture was cooled to ambient temperature and insoluble material removed by filtration. The filtrate was then extracted with aqueous sodium bicarbonate solution and the aqueous extracts carefully acidified with 48% hydrobromic acid. The precipitated solid was collected by filtration and dried under vacuum to give 4-bromomethyl-2-methylbenzoic acid (B) (3.92 g) as a white solid, m.p. 157°-160° C.; NMR (CDCl3): 2.66(s, 3H), 4.56(s, 2H), 7.2-7.35(complex m, 2H), 8.04(d, 1H).

Provenance & Evidence