Thionyl Chloride → (E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl chloride hydrochloride
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[CH2:16]O)=[CH:10][CH:9]=2)[CH:2]=1.S(Cl)([Cl:20])=O>C(Cl)Cl>[ClH:20].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[CH2:16][Cl:20])=[CH:10][CH:9]=2)[CH:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In 5 ml of methylene chloride was dissolved 300 mg of (E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl alcohol, and 0.58 ml of thionyl chloride was dropped into the resulting solution with ice-cooling, after which the resulting mixture was subjected to reaction under reflux for 30 minutes. The solvent and the excessive thionyl chloride were removed by distillation under reduced pressure, to obtain (E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl chloride hydrochloride as the residue. This was dissolved in 3 ml of N,N-dimethylformamide.