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

Temperature

-15 °C

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.

1. additionadded dropwise
2. extractionextracted with chloroform
3. extractionThe organic extract
4. dry with materialwas dried (sodium sulfate)
5. customevaporated
6. customto give a pale yellow oil, which
7. temperatureat reflux temperature for 24 hours
8. extractionConcentration of the reaction mixture followed by diethyl ether extraction and evaporation
9. customgave an orange-red oil, that
10. customThe solid that separated out
11. filtrationwas filtered
12. customdried by suction
13. customThe solid was recrystallized from diethyl ether

ORD record

ord-ec5c763e6fb54b21be25725941da1322

Source dataset

uspto-grants-1987_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04663344