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

HRID 536749Notes

Reaction equation

HRID 536749 reaction equation
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 77195Cyclopentanemethanol

Product 1

HCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonateYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of cyclopentylmethanol (2.5 g, 25 mmol), 4-methylbenzene-1-sulfonyl chloride (5.23 g, 27.5 mmol) in CH2Cl2 (50 mL) at 0° C. was treated with triethylamine (4.17 mL, 30 mmol) and the mixture was allowed to warm to room temperature for 8 hours. The mixture was then washed with water, brine, dried with anhydrous MgSO4 and concentrated under reduced pressure to afford 6.5 g the title compound. MS (DCI/NH3) m/z 272 (M+NH4)+.

Workup

  1. washThe mixture was then washed with water, brine
  2. dry with materialdried with anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07f9f6e79072470fa192ebee9ce3d7ff
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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