(4-(1H-Benzo[d]imidazol-2-yl)phenyl)methanol → 4-(1H-benzimidazol-2-yl)benzaldehyde

HRID 8968Notes

Reaction equation

HRID 8968 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1>C(Cl)Cl.C1COCC1.O=[Mn]=O>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1

Participants

5

Reactant 1

HCID 56965510(4-(1H-Benzo[d]imidazol-2-yl)phenyl)methanol

Product 1

HCID 219851714-(1H-benzimidazol-2-yl)benzaldehydeYield 42%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(Benzimidazol-2-yl)-benzyl alcohol from above (0.175 g, 0.78 mmol) was dissolved in CH2Cl2 (5 mL) and THF (8 mL), treated with activated MnO2 (0.68 g, 7.8 mmol) and stirred at room temperature for 1.5 h. The mixture was filtered through celite, the cake washed with CH2Cl2 and the solvent from the eluent removed under reduced pressure to afford 4-(benzimidazol-2-yl)-benzaldehyde (92 mg, 42%). 1H NMR (CD4OD) δ 7.28 (m, 2H), 7.60 (br, 1H (NH)), 7.65 (d, 2H, J=7.8 Hz), 8.09 (d, 2H, J=7.8 Hz), 8.30 (d, 2H, J=9.0 Hz), 10.08 (s, 1H (CHO)).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe cake washed with CH2Cl2
  3. customthe solvent from the eluent removed under reduced pressure

Sources & evidence

ORD record
ord-952b8ed9281d4331b9d03bfc456f033a
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Reaction notes

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