Dichloromethane → 2-Methoxy-3-octadecyloxypropyl methanesulfonate

HRID 231255

Reaction equation

HRID 231255 reaction equation
ClCCl.[CH3:4][O:5][CH:6]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:7][OH:8].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(N(CC)CC)C>[CH3:29][S:30]([O:8][CH2:7][CH:6]([O:5][CH3:4])[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 3364221-Propanol, 2-methoxy-3-(octadecyloxy)-

Product 1

HCID 145010372-Methoxy-3-octadecyloxypropyl methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 120 ml of dichloromethane are added 12.0 g of 2-methoxy-3-octadecyloxypropanol and 6.07 ml of triethylamine, to which 4.98 g of methanesulfonyl chloride is added dropwise with stirring under ice cooling. Thereafter, the mixture is stirred at room temperature for 2 hours to complete the reaction. The reaction mixture is then washed with water, an aqueous sodium bicarbonate solution and again water and dried over anhydrous sodium sulfate. The solvent is distilled off under reduced pressure to leave 14.6 g (100%) of the captioned compound.

Workup

  1. stirringThereafter, the mixture is stirred at room temperature for 2 hours
  2. customthe reaction
  3. washThe reaction mixture is then washed with water
  4. dry with materialan aqueous sodium bicarbonate solution and again water and dried over anhydrous sodium sulfate
  5. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-0463feb32d9745479a5b23a92d5682b6
Source dataset
uspto-grants-1989_07
Patent number
US04845219

Linked notes

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