Methanesulfonyl chloride → 2,5,8,11-Tetraoxatridecan-13-ol, 13-methanesulfonate

HRID 1440647Notes

Reaction equation

HRID 1440647 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14].[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[S:16]([O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:18])(=[O:17])[CH3:15]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 90263Tetraethylene glycol monomethyl ether

Product 1

HCID 147636792,5,8,11-Tetraoxatridecan-13-ol, 13-methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8.16 g (0.040M) of tetraethylene glycol monomethyl ether and 5.0 g (0.044M) of methanesulfonyl chloride in 100 ml of methylene chloride was stirred at 0° C. while 5.7 g (0.044M) of diisopropylethylamine was added dropwise so the temperature remained below 5° C. Stirring was continued at 0° C. for 20 minutes and the temperature was allowed to rise to room temperature over 2 hours. The solution was washed twice with an equal volume of water. It was then dried and concentrated to an oil, yielding 11 g (96%).

Workup

  1. additionwas added dropwise so the temperature
  2. customremained below 5° C
  3. waitto rise to room temperature over 2 hours
  4. washThe solution was washed twice with an equal volume of water
  5. customIt was then dried
  6. concentrationconcentrated to an oil
  7. customyielding 11 g (96%)

Sources & evidence

ORD record
ord-856cdcd5bbf44abeb622c14fe90cc969
Source dataset
uspto-grants-1996_03
Patent number
US05500338

Reaction notes

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