Thiophenol → 3-Chloropropyl phenyl sulfide

A solution of thiophenol (55.6 g, 0.505 mol) in aqueous sodium hydroxide (22.1 g, 0.55 mole in 200 mL water) was added over a period of 30 minutes to a cold stirred solution (chilled with an ice-water bath) of 1-bromo-3-chloropropane in 100 mL of dioxanes. After the addition was complete, the ice bath was removed and the mixture stirred at ambient temperature for 4.5 h. Water was added (200 mL) and the mixture extracted with hexane (2×300 mL portions). The combined extract was washed (water), dried (MgSO4) and concentrated to obtain an oil which was vacuum distilled at 85°-97° C. at 0.10 mmHg to obtain 22.38 g (89.5%) in 3 fractions.

1. additionAfter the addition
2. customthe ice bath was removed
3. additionWater was added (200 mL)
4. extractionthe mixture extracted with hexane (2×300 mL portions)
5. extractionThe combined extract
6. washwas washed (water)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customto obtain an oil which
10. distillationdistilled at 85°-97° C. at 0.10 mmHg
11. customto obtain 22.38 g (89.5%) in 3 fractions

ORD record

ord-b6a3372420b0433199717a5ab88388e0

Source dataset

uspto-grants-1992_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05140026