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

HRID 433325Notes

Reaction equation

HRID 433325 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.[OH:14][S:15]([O-:18])(=O)=O.[K+].[CH3:20]O>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:15]([CH3:20])(=[O:18])=[O:14])[CH2:5]2

Participants

5

Reactant 3

HCID 887MethanolHCID 516920Potassium bisulfateHCID 99207715-Chloro-2-methylsulfanylindan-1-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.5 g (2.35 mmol) of 5-chloro-2-methylsulfanylindan-1-one is dissolved in 10 ml of methanol; at 0° C., a solution of 4.33 g (7.05 mmol) of 2KHSO5×KHSO4×K2SO4 in 10 ml of water is added dropwise. The mixture is stirred at room temperature for 5 h; the methanol is distilled off and the aqueous residue is extracted with dichloromethane. The organic phase is separated off, dried over MgSO4, filtered and concentrated under reduced pressure. This gives 0.5 g of 5-chloro-2-methanesulfonylindan-1-one of melting point 197° C.

Workup

  1. distillationthe methanol is distilled off
  2. extractionthe aqueous residue is extracted with dichloromethane
  3. customThe organic phase is separated off
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-238b26a1f1c34f19adaee31e582da7c5
Source dataset
uspto-grants-2003_12
Patent number
US06667345B2

Reaction notes

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