4-Toluenesulfonyl chloride → Cyclopentylmethyl 4-methylbenzene-1-sulfonate

HRID 1838946Notes

Reaction equation

HRID 1838946 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH:12]1([CH2:17][OH:18])[CH2:16][CH2:15][CH2:14][CH2:13]1.[OH-].[K+]>CCOCC.O>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:18][CH2:17][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 77195Cyclopentanemethanol

Product 1

HCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

p-Toluenesulphonyl chloride (2.12 g, 11.1 mmol) was added to a solution of cyclopentanemethanol (1 ml, 9.25 mmol) in ether (25 ml), and the solution cooled in an ice/salt bath. Freshly powdered potassium hydroxide (4.7 g, 83.3 mmol) was added and the reaction mixture allowed to warm to room temperature, over 2 hours. The reaction was diluted with water, the phases separated, and the aqueous layer extracted with ether. The combined organic solutions were dried (MgSO4), and evaporated under reduced pressure, to give the title compound as a clear oil, 2.18 g.

Workup

  1. temperaturethe solution cooled in an ice/salt bath
  2. customthe phases separated
  3. extractionthe aqueous layer extracted with ether
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1e04f027a5534845a0d52cb0fddcc0b8
Source dataset
uspto-grants-2004_01
Patent number
US06677335B1

Reaction notes

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