Acetic Acid → 4-Chloro-4'-methylsulfinylmethylbenzophenone

HRID 1421549Notes

Reaction equation

HRID 1421549 reaction equation
C(O)(=[O:3])C.[Cl:5][C:6]1[CH:22]=[CH:21][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][S:19][CH3:20])=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1.OO.O>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:22]=[CH:21][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][S:19]([CH3:20])=[O:3])=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 196893654-Chloro-4'-methylthiomethylbenzophenone

Product 1

HCID 187798984-Chloro-4'-methylsulfinylmethylbenzophenone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To an acetic acid solution (30 ml) of 4-chloro-4'-methylmercaptomethylbenzophenone (8.3 g), aqueous 30% hydrogen peroxide solution (3.5 ml) was added, and the mixture was stirred for 2 hours while keeping at 10° C. To the reaction solution, water (200 ml) and toluene (200 ml) were added, and then the organic layer was separated, and washed successively with water, an aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, followed by drying over anhydrous magnesium sulfate. After distilling off the solvent, the crude product was purified by silicagel column chromatography (developing solvent: acetone:n-hexane=50:50) to obtain 4-chloro-4'-methylsulfinylmethylbenzophenone (5.3 g).

Workup

  1. customwhile keeping at 10° C
  2. customthe organic layer was separated
  3. washwashed successively with water
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe crude product was purified by silicagel column chromatography (developing solvent: acetone:n-hexane=50:50)

Sources & evidence

ORD record
ord-58a95c505ef64091ab67e802b8809380
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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