Pyridine → 2-Methylcyclopentyl 4-methylbenzene-1-sulfonate

HRID 128556Notes

Reaction equation

HRID 128556 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[OH:7].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.N1C=CC=CC=1>O>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:7][CH:3]2[CH2:4][CH2:5][CH2:6][CH:2]2[CH3:1])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 322052-Methylcyclopentanol

Product 1

HCID 127684732-Methylcyclopentyl 4-methylbenzene-1-sulfonateYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Methylcyclopentanol (21.06 g, 0.210 mol) and p-toluenesulfonyl chloride (48.3 g, 0.252 mol) were charged into a 500 cc three-necked flask equipped with a stirrer, and then pyridine (170 ml) was added dropwise thereto under ice-cooling. The mixture was stirred for 10 hours while gradually elevating the temperature to room temperature. After completion of the reaction, cold water (500 ml) was added to the reaction mixture, and the mixture was extracted with ether (200 ml×3). The organic layers were combined, washed successively with 2N hydrochloric acid, water and a saturated aqueous solution of sodium chloride, and dried with anhydrous magnesium sulfate. The drying agent was separated by filtration, and the solvent was distilled off under reduced pressure to obtain substantially pure 2-methylcyclopentyl p-toluenesulfonate as a colorless transparent oily substance (49.7 g, 0.195 mol, 93% yield).

Workup

  1. customequipped with a stirrer
  2. temperatureunder ice-cooling
  3. customto room temperature
  4. additionwas added to the reaction mixture
  5. extractionthe mixture was extracted with ether (200 ml×3)
  6. washwashed successively with 2N hydrochloric acid, water
  7. dry with materiala saturated aqueous solution of sodium chloride, and dried with anhydrous magnesium sulfate
  8. customThe drying agent was separated by filtration
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cb3eae935fa244b188736afdb85bb54f
Source dataset
uspto-grants-1995_11
Patent number
US05464811

Reaction notes

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