Hydrochloric Acid → 2-(m-Methylbenzylthio)-5-trifluoromethylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of m-methylbenzylmercaptan (3.36 g, 24.3 mmol), sodium methoxide (1.31 g, 24.3 mmol) and N,N-dimethylformamide (12.5 ml) was cooled to -15° C., and then added dropwise with stirring to a solution of 4-chloro-3-cyanobenzotrifluoride (5.0 g, 2.43 mmol), in N,N-dimethylformamide (7.5 ml). After stirring for 1 hour at room temperature under a nitrogen atmosphere, the mixture was added to cold water (175 ml) and extracted with chloroform. The organic extract was dried (sodium sulfate) and evaporated to give a pale yellow oil, which was taken up in ethanol (10 ml) and 20% aqueous sodium hydroxide (45 ml) and heated at reflux temperature for 24 hours. Concentration of the reaction mixture followed by diethyl ether extraction and evaporation gave an orange-red oil, that was suspended in water and acidified with 6N hydrochloric acid. The solid that separated out was filtered and dried by suction. The solid was recrystallized from diethyl ether; yield 5.95 g (75%). The 60 MHz NMR spectrum in chloroform-d was in accord with the desired structure.

Provenance & Evidence