Thiophenol → 3-Chloropropyl phenyl sulfide

A mixture of 54.0 g (490 mmols) of thiophenol, 160.0 g (1016 mmols) of 1-bromo-3-chloropropane and 250 ml of a 2.2 M aqueous sodium hydroxide solution was heated under reflux for 30 hours. After cooling, the reaction mixture was extracted with methylene chloride. The methylene chloride layer was washed with an aqueous dil. sodium hydroxide solution and then with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was distilled under reduced pressure (138 -140° C./13 mmHg) to afford 51.9 g (yield: 57%) of the title compound.

1. temperaturewas heated
2. temperatureunder reflux for 30 hours
3. temperatureAfter cooling
4. extractionthe reaction mixture was extracted with methylene chloride
5. washThe methylene chloride layer was washed with an aqueous dil. sodium hydroxide solution
6. dry with materialwith water and dried over anhydrous sodium sulfate
7. customThe solvent was evaporated under reduced pressure
8. distillationthe residue was distilled under reduced pressure (138 -140° C./13 mmHg)

ORD record

ord-a14400083615456a9ac4f8bcdddcacb2

Source dataset

uspto-grants-1991_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05053408