Water → Ethyl (3-{3-[(methylsulfonyl)oxy]propyl}phenoxy)acetate

HRID 2389339Notes

Reaction equation

HRID 2389339 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][CH:17]=1)[O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH3:18][S:19](Cl)(=[O:21])=[O:20].O>C(Cl)Cl>[CH3:18][S:19]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][CH:17]=1)[O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 86637895Ethyl [3-(3-hydroxypropyl)phenoxy]acetate

Product 1

HCID 86637907Ethyl (3-{3-[(methylsulfonyl)oxy]propyl}phenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl [3-(3-hydroxypropyl)phenoxy]acetate (107.4 g) in DCM (1.07 L) was added TEA (113 mL) at ambient temperature. Methanesulfonyl chloride (45.4 mL) was added dropwise to the mixture at 0° C. The mixture was stirred for 1 hour at ambient temperature and water (1 L) was added to the mixture at the same temperature. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford ethyl (3-{3-[(methylsulfonyl)oxy]propyl}phenoxy)acetate (155.5 g) as a yellow oil.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a9321fd5737c4d248f7349700d35d2ba
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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