Toluene → 2-(1-Chloroethyl)-4-methoxy-pyridine hydrochloride

Reaction equation

S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH:13](O)[CH3:14])[CH:8]=1.C1(C)C=CC=CC=1>ClCCl>[ClH:3].[Cl:3][CH:13]([C:9]1[CH:8]=[C:7]([O:6][CH3:5])[CH:12]=[CH:11][N:10]=1)[CH3:14]

Participants

Procedure

36 ml of thionyl chloride are added dropwise to a cooled suspension of 57 g of (±)-1-[4-methoxy-2-pyridyl]ethanol in 400 ml of dichloromethane, in such a way that the internal temperature does not exceed 15° C. The mixture is then heated under reflux for 2.5 h, treated with 300 ml of toluene and concentrated to 150 ml. The reaction product which has precipitated is filtered off with suction and rinsed with cold toluene and petroleum ether. This gives 76.4 g (98.2%) of the title compound of m.p. 113°-116° C.