Réaction #2196

ord-27d91eecd20e450da1b8e17f791b0eaa

Équation de réaction

CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1
4-chloro-4'-methylthiomethylbenzophenone
CO
methanol
[Na+].[O-][I+3]([O-])([O-])[O-]
Sodium periodate
CS(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1
desired product
Rendement 93.0%
CS(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1
4-Chloro-4'-methylsulfinylmethylbenzophenone
Rendement 93.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwas added to this solution
  2. 2
    ConcentrationThe reaction mixture was concentrated
  3. 3
    workup.ADDITIONwater was added
  4. 4
    ExtractionThe mixture was extracted with ethyl acetate
  5. 5
    LavageThe ethyl acetate layer was washed with water
  6. 6
    Séchagedried over anhydrous magnesium sulfate
  7. 7
    workup.DISTILLATIONEthyl acetate was distilled off under reduced pressure
  8. 8
    LavageThe residual solid was washed with n-hexane

Mode opératoire

4-chloro-4'-methylthiomethylbenzophenone (4.2 g) was added to methanol (150 ml). Sodium periodate (3.6 g) dissolved in water (20 ml), was added to this solution, and the mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated, and water was added thereto. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with n-hexane to obtain the desired product (4.1 g, melting point: 116° to 118° C., yield: 93%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05728699uspto-grants-1998_03