Cyclopentanol → Cyclopentyl 4-methylbenzene-1-sulfonate

HRID 128549Notes

Reaction equation

HRID 128549 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[OH-].[K+]>CCOCC>[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium Hydroxide

Product 1

HCID 317685Cyclopentyl 4-methylbenzene-1-sulfonateYield 81.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cyclopentanol (10 g, 0.116 mol), p-toluenesulfonyl chloride (24.3 g, 0.128 mol) and ether (100 ml) were charged into a 200 cc round-bottom flask and dissolved. Then, potassium hydroxide (32.5 g, 0.58 mol) in a powder form was added slowly thereto while cooling below 10° C. in a water bath. After addition, the mixture was stirred as it was for additional 2 hours. After completion of the reaction, the mixture was poured into ice-water (20 ml), and the organic layer and the aqueous layer were separated. The organic layer was dried, and concentrated under reduced pressure to obtain cyclopentyl p-toluenesulfonate as a pale yellow viscous liquid (22.0 g, 81.8% yield).

Workup

  1. dissolutiondissolved
  2. temperaturewhile cooling below 10° C. in a water bath
  3. additionAfter addition
  4. customAfter completion of the reaction
  5. customthe organic layer and the aqueous layer were separated
  6. customThe organic layer was dried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10bd3117be9e4d6fa0a66f25ae8a8113
Source dataset
uspto-grants-1995_11
Patent number
US05464811

Reaction notes

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