m-Chloroperbenzoic acid → 4-Chloro-4'-methylsulfonylmethylbenzophenone

HRID 1421550Notes

Reaction equation

HRID 1421550 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15]([CH3:17])=[O:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>ClCCl>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15]([CH3:17])(=[O:28])=[O:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 187798984-Chloro-4'-methylsulfinylmethylbenzophenone

Product 1

HCID 187799134-Chloro-4'-methylsulfonylmethylbenzophenoneYield 58.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-4'-methylsulfinylmethylbenzophenone (2.9 g) and m-chloroperbenzoic acid (2.5 g) were dissolved in dichloromethane, and the mixture was stirred for 12 hours at 0° C. After the precipitated crystals were filtered off, the filtrate was successively washed with aquous sodium bicarbonate solution, aqueous 5% sodium thiosulfate solution and water, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:5) to obtain 4-chloro-4'-methylsulfonylmethylbenzophenone (1.8 g).

Workup

  1. filtrationAfter the precipitated crystals were filtered off
  2. washthe filtrate was successively washed with aquous sodium bicarbonate solution, aqueous 5% sodium thiosulfate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:5)

Sources & evidence

ORD record
ord-ae7b094ee77040a8bb97d34f87210c1d
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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