4-Toluenesulfonyl chloride → 3-(Ethylsulfonyl)propyl 4-methylbenzenesulfonate

HRID 411158Notes

Reaction equation

HRID 411158 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][CH2:8][OH:9])(=[O:5])=[O:4])[CH3:2].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(Cl)Cl>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:9][CH2:8][CH2:7][CH2:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 129433033-(Ethanesulfonyl)propan-1-ol

Product 1

HCID 218676643-(Ethylsulfonyl)propyl 4-methylbenzenesulfonateYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(ethylsulfonyl)-1-propanol (from step (i) above; 13.4 g, 88 mmol) and p-toluenesulfonyl chloride (16.8 g, 88 mmol) in DCM (150 mL) was treated with TEA (13.4 g, 132 mmol), added dropwise. The resulting mixture was stirred at rt for 3h before being washed with aqueous ammonium chloride solution. The organic layer was then separated, dried and concentrated in vacuo. The product was crystallised from ether containing a small amount of DCM to yield 17.9 g (66%) of the title compound.

Workup

  1. additionadded dropwise
  2. washbefore being washed with aqueous ammonium chloride solution
  3. customThe organic layer was then separated
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe product was crystallised from ether containing a small amount of DCM

Sources & evidence

ORD record
ord-7493d6b56489442ebc59bf67be67f587
Source dataset
uspto-grants-2003_05
Patent number
US06559143B1

Reaction notes

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