Tetraethylene Glycol → 1,11-Bis(methanesulfonyloxy)-3,6,9-trioxandecane
Reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>O>[S:22]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][O:13][S:22](=[O:24])(=[O:23])[CH3:21])(=[O:24])(=[O:23])[CH3:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A 5,000 mL, 3-necked flask equipped with a mechanical stirrer, thermometer and 500 mL addition funnel was charged with tetraethylene glycol (388 g, 2.0 mol) dichloromethane (1,500 mL) and triethylamine (445 g, 4.40 mol). The mixture was stirred and cooled to ca. 5° C., and methanesulfonyl chloride (470 g, 4.1 mol) was added dropwise over 3 hours. The reaction mixture was stirred an additional 3 hours while warming to 25° C., then water (1,000 mL) was added and the phases were separated. The organic layer was washed with ice-cold 6 N HCl (2×1,000 mL) and then washed with 5% Na2CO3, saturated aqueous NaCl, dried, filtered and evaporated in vacuo to yield 627 g (90%) of tetraethylene glycol dimesylate, i.e.,
Workup
- customA 5,000 mL, 3-necked flask equipped with a mechanical stirrer
- additionthermometer and 500 mL addition funnel
- stirringThe reaction mixture was stirred an additional 3 hours
- temperaturewhile warming to 25° C.
- customthe phases were separated
- washThe organic layer was washed with ice-cold 6 N HCl (2×1,000 mL)
- washwashed with 5% Na2CO3, saturated aqueous NaCl
- customdried
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-d18027070c704b96bb52063f604f8596
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04436664
Reaction notes
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