4-Toluenesulfonyl chloride → 3-Chloropropyl p-toluenesulfonate

HRID 902720Notes

Reaction equation

HRID 902720 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][OH:5].[S:6](Cl)([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(=[O:8])=[O:7]>N1C=CC=CC=1.O>[S:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(=[O:8])=[O:7]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 123133-Chloro-1-propanol

Product 1

HCID 694343-Chloropropyl p-toluenesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 3-chloro-1-propanol (1.88 g, 20 mmole) in 20 ml of pyridine was treated at 0° with tosyl chloride (7.6 g, 40 mmole). The solution was warmed to 23°, and stirred 16 hours. The reaction was diluted with 100 mL of H2O and stirred for 90 minutes, and extracted with Et2O. The extracts were washed with 1N HCl, dried, and the solvents thoroughly removed, and gave the titled product, 2.3 g (46%). MS (ESI) 188 (MH+).

Workup

  1. temperatureThe solution was warmed to 23°
  2. stirringstirred for 90 minutes
  3. extractionextracted with Et2O
  4. washThe extracts were washed with 1N HCl
  5. customdried
  6. customthe solvents thoroughly removed

Sources & evidence

ORD record
ord-2e0a2bb4065b47a0ace90b4fc7edbe3c
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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