1-butyl-1H-benzotriazole-5-methanol → butyl-1H-benzotriazole-5-carboxaldehyde

HRID 2248318Notes

Reaction equation

HRID 2248318 reaction equation
[CH2:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][OH:15])=[CH:13][C:8]=2[N:7]=[N:6]1)[CH2:2][CH2:3][CH3:4]>[O-2].[Mn+4].[O-2].ClCCl>[CH2:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14]=[O:15])=[CH:13][C:8]=2[N:7]=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 149905701-butyl-1H-benzotriazole-5-methanol

Product 1

HCID 14990615butyl-1H-benzotriazole-5-carboxaldehydeYield 42.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 36.5 parts of 1-butyl-1H-benzotriazole-5-methanol, 35 parts of manganese(IV) oxide and 390 parts of dichloromethane was stirred for 12 hours at room temperature. The manganese(IV) oxide was filtered off over diatomaceous earth and another portion of 35 parts of manganese(IV) oxide was added to the filtrate. After stirring for 12 hours at room temperature, the whole was filtered and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using dichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 15.3 parts (42.2%) of 1-butyl-1H-benzotriazole-5-carboxaldehyde as a residue (int. 57).

Workup

  1. filtrationThe manganese(IV) oxide was filtered off over diatomaceous earth
  2. additionanother portion of 35 parts of manganese(IV) oxide was added to the filtrate
  3. stirringAfter stirring for 12 hours at room temperature
  4. filtrationthe whole was filtered
  5. customthe filtrate was evaporated
  6. customThe residue was purified by column chromatography over silica gel
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated

Sources & evidence

ORD record
ord-c98446bee9824a3c93965697442dbc5c
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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