Potassium Permanganate → 4-Methoxy-8-nitro-dibenzo[b,d]furan-1-carboxylic acid

HRID 131586Notes

Reaction equation

HRID 131586 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=3[C:7]=2[C:6]([CH:19]=[O:20])=[CH:5][CH:4]=1.[Mn]([O-])(=O)(=O)=[O:22].[K+]>CC(C)=O.O.CC(C)=O>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=3[C:7]=2[C:6]([C:19]([OH:22])=[O:20])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 211057134-Methoxy-8-nitro-dibenzofuran-1-carbaldehyde

Product 1

HCID 211057144-Methoxy-8-nitro-dibenzo[b,d]furan-1-carboxylic acidYield 61.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
65 °C

Procedure

4-methoxy-8-nitro-1-formyl dibenzo[b,d]furan (1.1 gm, 0.0034 mol) in acetone (5 ml) was heated to 60-70° C. for 10 min. To the above suspension was added dropwise a hot solution of potassium permanganate (1.07 gm, 0.0068 mol) in water:acetone (1:3) (15 ml) for 10 min. The reaction was heated to 60-70° C. for 10 min., cooled to room temperature and filtered. The residue washed with acetone and the filterate was extracted with 10% sodium hydroxide solution. Acidification, followed by filteration and washing of the precipitate yielded 4-methoxy-8-nitro-dibenzo[b,d]furan-1-carboxylic acid (0.6 gm) as white solid; mp: 178° C. (dec.)

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe residue washed with acetone
  4. extractionthe filterate was extracted with 10% sodium hydroxide solution
  5. washwashing of the precipitate

Sources & evidence

ORD record
ord-6f0cc9c0e0da4f5e9f506c501e0a7c68
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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