Hydrogen Peroxide → 2-Butyl-5-formylimidazole

HRID 1637368Notes

Reaction equation

HRID 1637368 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH2:10][OH:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[Bi].[OH-].[Na+].OO>[Pt]>[CH2:1]([C:5]1[NH:6][C:7]([CH:10]=[O:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 27356732-Butyl-5-hydroxymethylimidazoleHCID 5359367Bismuth

Product 1

HCID 27356712-Butyl-5-formylimidazoleYield 98.2%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

4.0 g of 2-n-butyl-5-hydroxymethylimidazole, 0.6 g of 5 percent platinum and 5 percent bismuth on activated carbon (comprising 61.3 percent water), and 25.6 ml of 1N NaOH solution were heated to about 60° C. with stirring. At 60° to 64° C., 6.8 g of 15 percent strength aqueous H2O2 solution was added dropwise over the course of 45 min. The reaction mixture was then allowed to react for 15 min and then filtered off. The pH of the filtrate was adjusted from 13.2 to 9.0 using 20 percent H2SO4, as a result of which a yellow suspension formed. This was cooled, and the crude product was able to be filtered off and/or extracted with methylene chloride. The reaction was monitored by GC analysis. The reaction yield was 98.2 percent (1.8 percent of starting material).

Workup

  1. customto react for 15 min
  2. filtrationfiltered off
  3. customas a result of which a yellow suspension
  4. customformed
  5. temperatureThis was cooled
  6. filtrationto be filtered off
  7. extractionextracted with methylene chloride
  8. customThe reaction yield was 98.2 percent (1.8 percent of starting material)

Sources & evidence

ORD record
ord-d071eefbba0447d9a4f107aac4d31956
Source dataset
uspto-grants-2000_03
Patent number
US06040457

Reaction notes

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