Water → HCID 178467220, compound

HRID 1413303Notes

Reaction equation

HRID 1413303 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.O.CC1[NH:25][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:23][C:22]=1CO>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:26]1([C:24]2[NH:23][CH:22]=[C:1]([C:2]([CH3:4])=[O:3])[N:25]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 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⟧ sulfuric 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.) Removal of the methylene chloride

Sources & evidence

ORD record
ord-7c72a3f799d645e397a4a9988e7dd095
Source dataset
uspto-grants-1981_02
Patent number
USRE030511

Reaction notes

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