반응 #1467733

반응 방정식

4-Chloro-1-(4-methoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid

dichloromethane

aluminum chloride

→

4-chloro-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid

수율 83.1%

용매

ethanol

반응 조건

후처리

1. 1
   workup.DISSOLUTIONdissolved once
2. 2
   기타a precipitate separated out
3. 3
   workup.ADDITION50 ml of acetone and 20 ml of water were added to the precipitate
4. 4
   workup.ADDITIONTo the resulting solution was added 20 ml of lN-hydrochloric acid
5. 5
   기타to give a precipitate, which
6. 6
   세척the column was washed with 75% ethanol
7. 7
   workup.ADDITIONdiluted with water to the ethanol concentration of 50%

실험 절차

4-Chloro-1-(4-methoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid (15 g) was added to 270 ml of a dichloromethane solution containing 16.2 g of aluminum chloride and 10 g of 1,3-ethanedithiol and the mixture was stirred at room temperature, whereupon the starting material dissolved once and then a precipitate separated out. The mixture was allowed to stand at room temperature for 6 hours. The supernatant was then discarded, and 50 ml of acetone and 20 ml of water were added to the precipitate. To the resulting solution was added 20 ml of lN-hydrochloric acid to give a precipitate, which was dissolved in 150 ml of 75% ethanol. The solution was passed through a column of 50 ml of Amberlite IRC-50 (trademark) (H-form) and the column was washed with 75% ethanol. The effluent and washings were combined and diluted with water to the ethanol concentration of 50%. The above procedure gave 12 g of 4-chloro-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid as colorless scales, m.p. 190°-192 ° C. (decompn.).

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