Triethylamine → 1,2-Bis(methanesulfonyloxymethyl)cyclohexane, (1R,2R)-

HRID 1956747Notes

Reaction equation

HRID 1956747 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[CH2:9][OH:10].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)(Cl)Cl>[CH3:18][S:19]([O:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[CH2:9][O:10][S:19]([CH3:18])(=[O:21])=[O:20])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11217323rel-(1R,2R)-1,2-Cyclohexanedimethanol

Product 1

HCID 2534831,2-Bis(methanesulfonyloxymethyl)cyclohexane, (1R,2R)-Yield 59.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the compound (2) (71.86 g; 0.499 mol) and triethylamine (151.21 g; 1.497 mol) in chloroform (1 liter), methanesulfonyl chloride (114.27 g; 0.998 mol) is dropwise added under ice-cooling, and the resultant mixture is stirred at room temperature for 6 hours. The reaction mixture is washed with water, dried and concentrated under reduced pressure. Diethyl ether is added to the residue for crystallization, and the precipitated crystals are collected to give trans-1,2-bis(methanesulfonyloxymethyl)cyclohexane (3) (88.57 g).

Workup

  1. temperaturecooling
  2. washThe reaction mixture is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. additionDiethyl ether is added to the residue for crystallization
  6. customthe precipitated crystals are collected

Sources & evidence

ORD record
ord-f24053383d72449f84808df8cdc9b6fb
Source dataset
uspto-grants-1998_07
Patent number
US05780632

Reaction notes

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