Hydrogen Peroxide → HCID 20300557, compound

HRID 2167230Notes

Reaction equation

HRID 2167230 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]=C)[C:9]=1[CH3:17].FC(F)(F)C(C)=O.OO>O.ClCCl.C(#N)C.C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=O.[Na+].[Na+]>[CH3:17][C:9]1[C:8]([CH3:7])=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:14][CH:15]1[CH2:1][O:4]1

Participants

9

Reactant 4

HCID 784Hydrogen PeroxideHCID 9871Methyl trifluoromethyl ketoneHCID 11430Potassium CarbonateHCID 206267321,2-Dimethyl-3-(prop-2-en-1-yl)benzene2×

Product 1

HCID 20300557HCID 20300557, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 8759EDTA disodium saltCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A buffer was prepared by dissolving K2CO3 (20.7 g) and EDTA-Na2 (11.5 mg) in water (100 mL). 1,2-Dimethyl-3-(2-propenyl)benzene, compound of formula (XXIII), prepared according to example 3 (0.90 g, 6.16 mmol), was dissolved in a mixture of dichloromethane and acetonitrile (vv 1:1, 60 mL), and the buffer prepared as described above (9.3 mL) was added. To the resulting mixture, first 1,1,1-trifluoroacetone (60 μL) and then hydrogen peroxide (30% in water, 6.2 mL, 60.7 mmol) were added and the mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water (100 mL), the organic phase was separated, and the aqueous phase was extracted with dichloromethane (2 times with 50 mL each). The combined organic phases were dried over Na2SO4, concentrated under reduced pressure, and the residue was purified by via silica gel column chromatography using hexane:ethyl acetate as eluent (vv 32:1) to give 851 mg (85%) of the title compound.

Workup

  1. customA buffer was prepared
  2. customthe buffer prepared
  3. additionwas added
  4. customthe organic phase was separated
  5. extractionthe aqueous phase was extracted with dichloromethane (2 times with 50 mL each)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by via silica gel column chromatography

Sources & evidence

ORD record
ord-b60db02b967646a7833302369b44abb2
Source dataset
uspto-grants-2015_06
Patent number
US09045433B2

Reaction notes

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