Potassium Permanganate → 4-Difluoromethoxy-8-nitrodibenzo[b,d]furan-1-carboxylic acid

HRID 1354359Notes

Reaction equation

HRID 1354359 reaction equation
[F:1][CH:2]([F:22])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=3[C:8]=2[C:7]([CH:20]=[O:21])=[CH:6][CH:5]=1.[Mn]([O-])(=O)(=O)=[O:24].[K+]>CC(C)=O.O>[F:22][CH:2]([F:1])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=3[C:8]=2[C:7]([C:20]([OH:24])=[O:21])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 211057104-Difluoro methoxy-8-nitro-1-formyl dibenzo[b,d]furan

Product 1

HCID 211057114-Difluoromethoxy-8-nitrodibenzo[b,d]furan-1-carboxylic acidYield 64.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

4-difluoromethoxy-8-nitro-1-formyl dibenzo[b,d]furan (150 mg, 0.48 mmol) in acetone (20 ml) and water (5 ml) was heated to 60–70° C. for 10 min. To the above solution was added dropwise a solution of potassium permanganate (150 mg, 0.973 mmol) in water (5 ml) for 10 min. The reaction was heated to 60–70° C. for 30 min., and filtered hot through celite bed. Acidification of the filterate resulted in a precipitate which on filteration and washing with water yielded 4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxylic acid (100 mg) as white solid; mp: >270° C.

Workup

  1. temperatureThe reaction was heated to 60–70° C. for 30 min.
  2. filtrationfiltered hot through celite bed
  3. customAcidification of the filterate resulted in a precipitate which on filteration
  4. washwashing with water

Sources & evidence

ORD record
ord-cce89832ed4a4fc686883c6f5ac54603
Source dataset
uspto-grants-2007_05
Patent number
US07223789B2

Reaction notes

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