Hydrogen Peroxide → (Methylsulfonyl)methyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate

HRID 1065527Notes

Reaction equation

HRID 1065527 reaction equation
[CH3:1][S:2][CH2:3][O:4][C:5](=[O:26])[CH:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)[CH3:7].OO.CC(C)=[O:31].[OH2:33]>[NH4+].[NH4+].[O-][Mo]([O-])(=O)=O>[CH3:1][S:2]([CH2:3][O:4][C:5](=[O:26])[CH:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][CH:17]=2)=[CH:13][CH:14]=1)[CH3:7])(=[O:31])=[O:33]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 12852222HCID 12852222, compoundHCID 18366337Propan-2-one--water (1/1)

Product 1

HCID 12852231(Methylsulfonyl)methyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate

Reagents, catalysts & solvents 1

HCID 61578Diammonium molybdateCatalyst

Procedure

40 g (0.096 mol) of 2-[p-[(α,α,α-trifluoro-p-tolyl)oxy]phenoxy]-propionic acid [(methylthio)methyl]ester are dissolved in 120 ml of acetone/water (5:1) and treated slowly with 192 ml of a 30% solution of hydrogen peroxide. 96 ml of ammonium molybdate solution (35.2 g of ammonium molybdate in 96 ml of water) are added dropwise to the mixture which is cooled with an ice-bath. The mixture is stirred at room temperature for 2 hours. It is then extracted several times with ether, the ether extract is washed with sodium dithionite solution and the solution is again washed neutral with eight 100 ml portions of saturated sodium chloride solution and subsequently with five 100 ml portions of water. The mixture is treated with active carbon, filtered and evaporated. The residue is recrystallised from methylene chloride/n-hexane. There is obtained 2-[p-[(α,α,α-trifluoro-p-tolyl)oxy]phenoxy]-propionic acid [(methylsulphonyl)methyl]ester which melts at 87°-88° C.

Workup

  1. temperatureis cooled with an ice-bath
  2. extractionIt is then extracted several times with ether
  3. extractionthe ether extract
  4. washis washed with sodium dithionite solution
  5. additionThe mixture is treated with active carbon
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is recrystallised from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-e10bdbc81b924998a94b8283b0e45f6c
Source dataset
uspto-grants-1982_05
Patent number
US04329488

Reaction notes

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