2-(Benzyloxy) ethanol → 2-Benzyloxyethyl mesylate

HRID 1603744Notes

Reaction equation

HRID 1603744 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>ClCCl.C(N(CC)CC)C>[CH3:12][S:13]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 121412-(Benzyloxy) ethanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 108572722-Benzyloxyethyl mesylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-(benzyloxy)ethanol in 320 ml of dichloromethane, 35 ml of triethylamine and 19.5 ml of methanesulfonyl chloride were added under ice cooling, followed by stirring at room temperature for 2 hours. The reaction mixture was added with ice water and then extracted with dichloromethane. After the extract was washed with a saturated solution of sodium chloride, the extract was dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, whereby 49 g of 2-(benzyloxy)ethyl methanesulfonate were obtained (yield: stoichiometric).

Workup

  1. extractionextracted with dichloromethane
  2. washAfter the extract was washed with a saturated solution of sodium chloride
  3. dry with materialthe extract was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-26a9a54b5b09499695ec5eb3ca57f1ee
Source dataset
uspto-grants-1999_11
Patent number
US05990139

Reaction notes

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