Thiophenol → 3-Chloropropyl phenyl sulfide

Participants

Reaction Steps

40 ml of an aqueous solution containing 6.0 g of thiophenol and 7.8 g of 3-bromo-1-chloropropane were subjected to reflux for 1 hour under heating. To the solution, 40 ml of aqueous solution of sodium hydroxide containing 2.4 g thereof were then fed dropwise. Then, the solution was further subjected to reflux for another 2 hours under heating, and the solution reacted was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer resulted was then washed with dilute aqueous alkaline solution and saturated saline solution in series, then dried with anhydrous magnesium sulfate. The solvent used was removed by distillation under reduced pressure, and the residue obtained was purified by using silica gel column chromatography, for which hexane was used for the developer, thereby affording 6.5 g of 1-chloro-3-phenylthio propane.

Provenance & Evidence