Thionyl Chloride → 4-(4-Chlorobutyl)pyridine

HRID 892460Notes

Reaction equation

HRID 892460 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10]O)=[CH:3][CH:2]=1.S(Cl)([Cl:14])=O>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][Cl:14])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27846554-Pyridinebutanol

Product 1

HCID 109539414-(4-Chlorobutyl)pyridineYield 90.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 4-(4-pyridinyl)-1-butanol (Mayer J. M. and Testa, B., Helv. Chim. Acta 65, pages 1868-1884 (1982)) (4.20 g, 27.7 mmol) in 30 mL of chloroform is cooled to 0° C. and treated with thionyl chloride (6.60 g, 55.54 mmol) in 30 mL of chloroform. The reaction is allowed to warm to room temperature over 15 hours. The volatiles are removed in vacuo. The residue is cooled to 0° C. and treated with 50 mL of cold 10% sodium hydroxide solution and the mixture is extracted with three 100-mL portions of chloroform. The combined organic extracts are dried over sodium sulfate and the solvents are removed under reduced pressure to give 4.25 g of 4-(4-pyridinyl)-1-butylchloride as a brown oil.

Workup

  1. customThe volatiles are removed in vacuo
  2. temperatureThe residue is cooled to 0° C.
  3. additiontreated with 50 mL of cold 10% sodium hydroxide solution
  4. extractionthe mixture is extracted with three 100-mL portions of chloroform
  5. dry with materialThe combined organic extracts are dried over sodium sulfate
  6. customthe solvents are removed under reduced pressure

Sources & evidence

ORD record
ord-92dd2d59e02d41eeaa805db3f77beb89
Source dataset
uspto-grants-1992_06
Patent number
US05118691

Reaction notes

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