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

Participants

Reaction Steps

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.

Provenance & Evidence