[2-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazol-4-yl]methanol → 2-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carbaldehyde

HRID 1698594Notes

Reaction equation

HRID 1698594 reaction equation
[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]=1

Participants

4

Reactant 1

HCID 58012349[2-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazol-4-yl]methanol

Product 1

HCID 580123672-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carbaldehydeYield 93%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 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.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography on alumina with a 50% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-f945ff047b284da5a074b7d22a793074
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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