2-Chlorobenzaldehyde → 1H-Imidazole, 1-hydroxy-4,5-dimethyl-2-phenyl-

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Reaction Steps

Chlorobenzaldehyde (160 mmol) was added to a suspended solution of 2,3-butanedione monoxime (240 mmol) in EtOH. After stirring for 30 minutes, 2,3-butanedione monoxime (240 mmol) and 112 mL of 28% ammonia water were added. The reaction mixture was stirred for 12 hours at room temperature. The mixture was concentrated under reduced pressure and the residue was diluted with methylene chloride. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel with an eluent of 5% MeOH in CH2Cl2 gave 19.3 g (64%) of 4,5-dimethyl-2-phenyl-1H-imidazol-1-ol as a white solid.

Provenance & Evidence