Thiophenol → 3-Chloropropyl phenyl sulfide

Participants

Reaction Steps

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.

Provenance & Evidence