Water → HCID 178467220, compound

HRID 2419751Notes

Reaction equation

HRID 2419751 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.O.CC1[NH:20][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:18][C:17]=1CO>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:21]1([C:19]2[NH:18][CH:17]=[C:1]([C:2]([CH3:4])=[O:3])[N:20]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 836581H-Imidazole-4-methanol, 5-methyl-2-phenyl-HCID 131709961Jones' reagent

Product 1

HCID 178467220HCID 178467220, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

Jones reagent [5 ml; a solution of chromium trioxide (10.3 g) is a mixture of sulfunic acid (8.7 ml) and water (30 ml)] is added at 0°-5° C over 1 hour to a solution of methyl-2-phenyl-4-imidazolemethanol (3.0 g, 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 2N 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 g), m.p. 158°-158.5° C.

Workup

  1. filtrationthe precipitated solid collected by filtration
  2. additionThe solid is treated with 2N 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-11f421cd69c84db9ad81a4a0e3a69490
Source dataset
uspto-grants-1978_08
Patent number
US04107307

Reaction notes

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