Thionyl Chloride → 1-(Chloromethyl)-4-(methylthio)benzene

Participants

Reaction Steps

4-Methylsulfanylbenzyl alcohol (30.5 g; 0.2 mol) was dissolved in dichloromethane (180 ml). A solution of thionyl chloride (23.8 g; 0.2 mol) in dichloromethane (120 ml) was added dropwise to the initial charge, which was kept under reflux. The reaction mixture was stirred under reflux for a further 2 h. The solution was cooled to room temperature, washed with H2O (2×250 ml), dried over Na2SO4 and concentrated. The oily residue (6) was purified by column chromatography (Al2O3, CH2Cl2).

Provenance & Evidence