4-Methylbenzenethiol → HCID 420617, compound

Participants

Reaction Steps

1.04 g (43.4 mmol) of NaH was dissolved in 40 ml of tetrahydrofuran at 0° C. To the resulting solution, 4 ml of 4-methylthiophenol dissolved in dry tetrahydrofuran was added slowly. The resultant mixture was stirred at an ambient temperature for 20 minutes and 8.0 g (31 mnol) of N-(2-bromoethyl)phthalimide obtained in step 1 dissolved in dry tetrahydrofuran was added. The mixture was stirred overnight at an ambient temperature and then refluxed for 2 hours. The reaction mixture was distilled under a reduced pressure to produce a residue, which was dissolved in dichloromethane. Then, the resultant solution was washed with water and with an aqueous sodium chloride solution. The organic layer was dried and dichloromethane was removed under a reduced pressure. The residue was recrystallized from a mixture of ethyl acetate/hexane to obtain 6.86 g of the title compound as a yellow solid. The solution remaining after the recrystallization was purified by column chromatography (eluent; ethyl acetate: hexane=1:6) to obtain additional 1.40 g of the title compound. Therefore, a total of 8.26 g (yield 90%) of the title compound was obtained.

Provenance & Evidence