Thionyl Chloride → (E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl chloride hydrochloride

HRID 569154Notes

Reaction equation

HRID 569154 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]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15594566(E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl alcohol

Product 1

HCID 14099894(E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. additionwas dropped into the resulting solution with ice-
  2. temperaturecooling
  3. customafter which the resulting mixture was subjected to reaction
  4. temperatureunder reflux for 30 minutes
  5. customThe solvent and the excessive thionyl chloride were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-aab4e4478f1d43b385b6f221aaa2d26c
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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