Sodium Hydroxide → HCID 57687198, compound

HRID 1443464Notes

Reaction equation

HRID 1443464 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.Cl[CH2:11][CH2:12][S:13](Cl)(=[O:15])=[O:14].[OH-].[Na+]>CC(C)=O.ClC(Cl)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:13]([CH:12]=[CH2:11])(=[O:15])=[O:14])=[C:4]([CH3:9])[CH:3]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 148554-Chloro-2-methylphenolHCID 15385Ethanesulfonylchloride, 2-chloro-

Product 1

HCID 57687198HCID 57687198, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred mixture of 4-chloro-2-methylphenol (24.7 g, 173 mmol) in acetone (10 ml), dichloroethane (25 ml) and water (45 ml) at 0-5° C. was added drop wise simultaneously 2-chloro-1-ethane sulfonyl chloride (28.2 g, 173 mmol) and a solution of 25% sodium hydroxide (60 g) during approximately one hour. The mixture was stirred for one hour at Sand for one hour at room temperature. Water was added and the mixture was extracted twice with DCM. The organic phase was dried with sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with hexane-ethyl acetate which gave the title compound (33.4 g, 83%).

Workup

  1. extractionthe mixture was extracted twice with DCM
  2. dry with materialThe organic phase was dried with sodium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluted with hexane-ethyl acetate which

Sources & evidence

ORD record
ord-b3a70251067c4233bc75ad0ff35acea6
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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