Cyclohexanemethanol → Cyclohexylmethyl methanesulfonate

HRID 1069187Notes

Reaction equation

HRID 1069187 reaction equation
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH:1]1([CH2:7][O:8][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7507CyclohexanemethanolHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 19963751Cyclohexylmethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Cyclohexylmethanol (1.25 mL, 10.0 mmol) was dissolved in CH2Cl2 (50 mL), treated with diisopropylethylamine (7.0 mL, 40.0 mmol), cooled to 0° C., treated with methanesulfonyl chloride (0.85 mL, 11.0 mmol), and stirred for 1 hour at room temperature. The reaction was diluted with CH2Cl2 (200 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated to give 2.42 g (125% crude yield) of the desired product which was used immediately without purification.

Workup

  1. washwashed with saturated bicarbonate solution and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-dad42d38ce9c42868d5ebf773db416e3
Source dataset
uspto-grants-2001_06
Patent number
US06251919B1

Reaction notes

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