Isopropylethanediol → 2-Isopropoxyethyl Methanesulfonate

HRID 323473Notes

Reaction equation

HRID 323473 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][OH:7])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[S:16]([O:7][CH2:6][CH2:5][O:4][CH:1]([CH3:3])[CH3:2])(=[O:18])(=[O:17])[CH3:15]

Participants

5

Reactant 3

HCID 7996IsopropylethanediolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 184650452-Isopropoxyethyl Methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Alternately, combine 2-isopropoxyethanol (5.0 g, 48 mmol) and dichloromethane (50 mL). Cool in an ice bath. Add triethylamine (10.7 g, 105 mmol). Add dropwise methanesulfonyl chloride (1.43 g, 9.6 mmol). After 2 hours, dilute the reaction mixture with dichloromethane and extract with 1 M hydrochloric acid solution, a saturated aqueous solution of sodium bicarbonate, and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Distill the residue at reduced pressure to give 2-(isopropoxy)ethyl mesylate.

Workup

  1. temperatureCool in an ice bath
  2. extractionextract with 1 M hydrochloric acid solution
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue
  7. distillationDistill the residue at reduced pressure

Sources & evidence

ORD record
ord-5247ff734e8b462ebb95041a3a668059
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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