Thionyl Chloride → 3-(6-Chlorohexyl)pyridine

HRID 1583420Notes

Reaction equation

HRID 1583420 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]O)[CH:2]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:16])[CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 36861733-Pyridinehexanol

Product 1

HCID 135575283-(6-Chlorohexyl)pyridineYield 84.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 22 g of 6-(3-pyridyl)hexanol in 100 ml of chloroform was cooled in an ice bath and treated with a solution of 21.9 g of thionyl chloride in 50 ml of chloroform. The reaction mixture was allowed to warm to room temperature over 1 hour, was heated to a bath temperature of 60° C. for 1 hour and was concentrated. The residue was taken up in chloroform, washed with saturated potassium carbonate, dried, and evaporated. The residue was distilled to give 20.5 g (84%) of 6-(3-pyridyl)hexylchloride, bp 180°-190° C./0.15 mm.

Workup

  1. temperaturewas heated to a bath temperature of 60° C. for 1 hour
  2. concentrationwas concentrated
  3. washwashed with saturated potassium carbonate
  4. customdried
  5. customevaporated
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-f7a958daaa9245bdb1e241558991dd6a
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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