Ethanol → 5-Chloro-2-methylsulfonylindan-1-one

HRID 496694Notes

Reaction equation

HRID 496694 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6](SC)[CH2:5]2.[S:14]([O:18]OS([O-])(=O)=O)(O)(=O)=[O:15].[K+].OOS([O-])=O.[K+].[CH2:31](O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([S:14]([CH3:31])(=[O:18])=[O:15])[CH2:5]2

Participants

6

Reactant 4

HCID 702EthanolHCID 99207715-Chloro-2-methylsulfanylindan-1-oneHCID 23690007Potassium hydrogen persulfateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 99648205-Chloro-2-methylsulfonylindan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.5 g of 5-chloro-2-methylsulfanylindan-1-one was dissolved in 10 ml of dry ethanol. At 0° C., a solution of 4.33 g of potassium hydrogenpersulfate (2KHSO5xKHSO4xK2SO4; “Oxone”) in 10 ml of water was added dropwise and the reaction mixture was then stirred at room temperature for 5 h. The alcohol was distilled off under reduced pressure at room temperature. 20 ml of dichloromethane and 10 ml of water was added to the residue, and the mixture was stirred for 10 min. The organic phase was separated off, dried over magnesium sulfate, filtered and concentrated under reduced pressure, and the residue was dried. This gave 5-chloro-2-methylsulfonylindan-1-one of melting point 196° C.

Workup

  1. distillationThe alcohol was distilled off under reduced pressure at room temperature
  2. addition20 ml of dichloromethane and 10 ml of water was added to the residue
  3. stirringthe mixture was stirred for 10 min
  4. customThe organic phase was separated off
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was dried

Sources & evidence

ORD record
ord-535299d9ff2747788a555e8eb0114d53
Source dataset
uspto-grants-2005_09
Patent number
US06946492B2

Reaction notes

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