[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([CH3:27])[C:3]=1[O:4][C:5]1[N:9]([CH3:10])[C:8]2[C:11]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=[C:14]([CH2:15][OH:16])[C:7]=2[N:6]=1>[O-2].[Mn+4].[O-2].O1CCCC1>[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([CH3:27])[C:3]=1[O:4][C:5]1[N:9]([CH3:10])[C:8]2[C:11]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=[C:14]([CH:15]=[O:16])[C:7]=2[N:6]=1A mixture of [2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazol-4-yl]methanol (100 mg, 0.25 mmol), manganese(IV) oxide (428 mg, 4.92 mmol) and tetrahydrofuran (5 ml) was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on alumina with a 50% ethyl acetate/n-hexane to give 93 mg (0.23 mmol, 93%) of the title compound as a white powder.
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