Cyclohexanol → Cyclohexyl methanesulfonate

HRID 1095184Notes

Reaction equation

HRID 1095184 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][S:9](Cl)(=[O:11])=[O:10].C(N(CC)CC)C>C(Cl)Cl>[CH:1]1([O:7][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 85308Cyclohexyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of cyclohexanol (Aldrich, 10.2 g, 100 mmol) in methylene chloride (250 mL) at 0° C., Methane sulfonyl chloride (8.52 mL, 110 mmol) and triethyl amine (17.5 mL, 125 mmol) were added slowly and the mixture was stirred for 2 hrs. The reaction was quenched with water and the mixture was washed with 0.5 N HCl and brine solution. The organic layer was dried with sodium sulfate. Removal of solvent gave a yellow oil. 18.05 g.

Workup

  1. customThe reaction was quenched with water
  2. washthe mixture was washed with 0.5 N HCl and brine solution
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. customRemoval of solvent
  5. customgave a yellow oil

Sources & evidence

ORD record
ord-d73bb65238094656849b92fa781b99b2
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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