Hydrogen Peroxide → 2-Butyl-5-formylimidazole

HRID 1637369Notes

Reaction equation

HRID 1637369 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].CO>[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

7

Reactant 4

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

Product 1

HCID 27356712-Butyl-5-formylimidazoleYield 94.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

4.4 g of 2-n-butyl-5-hydroxymethylimidazole (crude starting material, 90.4 percent), 0.6 g of 5 percent platinum and 5 percent bismuth on activated carbon (comprising 61.3 percent water), 25.6 ml of 1N NaOH solution and 5 ml of methanol 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. The pH of the filtrate was adjusted from 13.0 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 94.5 percent (3.5 percent of starting material).

Workup

  1. customto react for 15 min
  2. filtrationfiltered
  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 94.5 percent (3.5 percent of starting material)

Sources & evidence

ORD record
ord-36d2deeafdf042f4953cfbf73dcd4bd9
Source dataset
uspto-grants-2000_03
Patent number
US06040457

Reaction notes

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