Methanol → 4-Chloro-4'-methylsulfinylmethylbenzophenone

HRID 2100

Reaction equation

HRID 2100 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15][CH3:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.CO.I([O-])(=O)(=O)=[O:22].[Na+]>O>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15]([CH3:16])=[O:22])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 196893654-Chloro-4'-methylthiomethylbenzophenoneHCID 23667635Sodium periodate

Product 1

HCID 187798984-Chloro-4'-methylsulfinylmethylbenzophenoneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  1. additionwas added to this solution
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationEthyl acetate was distilled off under reduced pressure
  8. washThe residual solid was washed with n-hexane

Sources & evidence

ORD record
ord-27d91eecd20e450da1b8e17f791b0eaa
Source dataset
uspto-grants-1998_03
Patent number
US05728699

Linked notes

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