Water → Ethyl 2-(3-(((methylsulfonyl)oxy)methyl)phenoxy)acetate

HRID 1049389Notes

Reaction equation

HRID 1049389 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>C1COCC1>[CH3:23][S:24]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18367402Ethyl [3-(hydroxymethyl)phenoxy]acetate

Product 1

HCID 117759824Ethyl 2-(3-(((methylsulfonyl)oxy)methyl)phenoxy)acetateYield 102.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(3-(hydroxymethyl)phenoxy)acetate (2.00 g) and triethylamine (1.44 g) in THF (10 mL) was added methanesulfonyl chloride (1.31 g) at 0° C., and the mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.80 g) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5cf51e8058f941e7a591304989af5335
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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