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

HRID 348417Notes

Reaction equation

HRID 348417 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-3821b905d8644d8e96f04bfb2a4e242b
Source dataset
uspto-grants-2007_02
Patent number
US07176311B2

Reaction notes

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