(2-Methyl-1H-benzimidazol-4-yl)methanol → 1H-Benzimidazole-4-carboxaldehyde,2-methyl-(9CI)

HRID 1723111Notes

Reaction equation

HRID 1723111 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][OH:12])[C:4]=2[N:3]=1>[O-2].[Mn+4].[O-2].C(OCC)(=O)C>[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]=[O:12])[C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 20026664(2-Methyl-1H-benzimidazol-4-yl)methanol

Product 1

HCID 200266661H-Benzimidazole-4-carboxaldehyde,2-methyl-(9CI)Yield 35.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(a-3) A mixture of 10 parts of 2-methyl-1H-benzimidazole-4-methanol, 10 parts of manganese(IV) oxide and 180 parts of ethyl acetate was stirred for 19 hours at room temperature. The reaction mixture was filtered over diatomaceous earth and washed with a mixture of ethyl acetate and methanol (80:20 by volume). The filtrate was evaporated and the residue was crystallized from 2-butanone. The product was filtered off and dried, yielding 3.5 parts (35.2%) of 2-methyl-1H-benzimidazole-4-carboxaldehyde (int. 67).

Workup

  1. filtrationThe reaction mixture was filtered over diatomaceous earth
  2. washwashed with a mixture of ethyl acetate and methanol (80:20 by volume)
  3. customThe filtrate was evaporated
  4. customthe residue was crystallized from 2-butanone
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-f664c30654984e57bc5880aecc0f5139
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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