Water → Cyclopentylmethyl 4-methylbenzene-1-sulfonate

HRID 476958Notes

Reaction equation

HRID 476958 reaction equation
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.O>N1C=CC=CC=1>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 77195Cyclopentanemethanol

Product 1

HCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonateYield 87.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(Bromomethyl)cyclopentane was obtained by the following procedure. A solution of commercially available cyclopentanemethanol (20 g) in dry pyridine (220 ml) was stirred at 0° while 4-toluenesulfonyl chloride (42 g) was added. The mixture was stirred at 0° for two hours, and was then held without stirring at 4° overnight. It was then poured into water and the product was extracted into dichloromethane. The dichloromethane extract was washed with 10% (w/v) HCl solution, water, and brine in succession, and was then dried (MgSO4) and evaporated. There was thus obtained the desired intermediate compound, cyclopentylmethyl (4-methylphenyl)sulfonate (44.42 g, 87% yield) as a clear oil. Without further purification, this material was dissolved in dry DMF (175 ml). Lithium bromide (45.5 g) was then added with stirring. The mixture was heated to 45° for three hours, and then cooled to room temperature. The mixture was then diluted with pentane (800 ml), and washed with water (800 ml). The water layer was extracted with an additional portion of pentane (200 ml) and was discarded. The combined pentane layers were washed with water (1000 ml), and brine (200 ml) in succession, and then dried (MgSO4). The solvent was distilled away at atmospheric pressure, and the residue was then vacuum distilled. The desired (bromomethyl)cyclopentane (23.64 g, 83% yield) was obtained as a colorless mobile oil, distilling at 54°-55° at a pressure of 2000 Pascals (15 Torr).

Workup

  1. additionwas added
  2. stirringwithout stirring at 4° overnight
  3. extractionthe product was extracted into dichloromethane
  4. extractionThe dichloromethane extract
  5. washwas washed with 10% (w/v) HCl solution, water, and brine in succession
  6. dry with materialwas then dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-765ab19eeffc4f5cb8824c6dbd994498
Source dataset
uspto-grants-1989_12
Patent number
US04886800

Reaction notes

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