Hydrogen Peroxide → HCID 11424691, compound

HRID 730298Notes

Reaction equation

HRID 730298 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[OH:20]O>[Cl-].[Na+].O.C[Re](=O)(=O)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][N+:14]([O-:20])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 6344Dichloromethane2×HCID 303820HCID 303820, compound

Product 1

HCID 11424691HCID 11424691, compound

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

To the mixture of 4-[4-(tert-butyl)phenyl]pyridine (8.7 g, 41 mmol) and methyltrioxorhenium (VII) (Aldrich) (170 mg, 0.7 mmol) in a 100-mL round-bottomed flask was added CH2Cl2 (18 mL). The mixture was then treated with 12 mL of hydrogen peroxide (Aldrich) dropwise. The reaction was stirred at room temperature under nitrogen overnight. Methylene chloride and brine were then added, and the aqueous layer was extracted with CH2Cl2 (40 mL). The organic layer was dried over Na2SO4, concentrated in vacuo to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 228 (M+1).

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (40 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f50fbaef0154d2f80fbd037bb85fd14
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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