1H-Imidazole-4-methanol, 5-methyl-2-phenyl- → HCID 178467220, compound

HRID 1863423Notes

Reaction equation

HRID 1863423 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.CC1[NH:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:17][C:16]=1CO>S(=O)(=O)(O)O.O.CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:20]1([C:18]2[NH:17][CH:16]=[C:1]([C:2]([CH3:4])=[O:3])[N:19]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 2

HCID 836581H-Imidazole-4-methanol, 5-methyl-2-phenyl-HCID 131709961Jones' reagent

Product 1

HCID 178467220HCID 178467220, compound

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

Jones reagent [5 ml.; a solution of chromium trioxide (10.3 gm.) in a mixture of sulfuric acid (8.7 ml.) and water (30 ml.)] is added at 0°-5° C. over 1 hours to a solution of methyl-2-phenyl-4-imidazolemethanol (3.0 gm., 0.016 mole) in acetone (25 ml.). The temperature is allowed to rise to 20° C. for 30 minutes then water (150 ml.) is added. The mixture is stirred for 1 hour and the precipitated solid collected by filtration. The solid is treated with 2 N hydrochloric acid (15 ml.), stirred 5 minutes, and is then neutralized with 10% sodium hydroxide. The aqueous mixture is extracted with methylene chloride (3×75 ml.). Removal of the methylene chloride yields the ketone as a white crystalline solid (1.73 gm.), m.p. 158°-158.5° C.

Workup

  1. filtrationthe precipitated solid collected by filtration
  2. additionThe solid is treated with 2 N hydrochloric acid (15 ml.)
  3. stirringstirred 5 minutes
  4. extractionThe aqueous mixture is extracted with methylene chloride (3×75 ml.)
  5. customRemoval of the methylene chloride

Sources & evidence

ORD record
ord-c8d3f3ba81504b77a7a349aec2f1616a
Source dataset
uspto-grants-1979_09
Patent number
US04168964

Reaction notes

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