Permanganate → 5-Bromobenzo(1,3)dioxole-4-carboxylic acid

HRID 617414Notes

Reaction equation

HRID 617414 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[Br:7][C:8]1[CH:16]=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[C:9]=1[CH:17]=[O:18].[Mn]([O-])(=O)(=O)=[O:20]>O.CC(C)=O>[Br:7][C:8]1[CH:16]=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[C:9]=1[C:17]([OH:20])=[O:18]

Participants

6

Reactant 3

HCID 24401PermanganateHCID 516875Potassium PermanganateHCID 110316405-Bromo-1,3-benzodioxole-4-carboxaldehyde

Product 1

HCID 125141065-Bromobenzo(1,3)dioxole-4-carboxylic acidYield 53%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Potassium permanganate (1.03 g, 6.55 mmol) was dissolved in water (25 mL). 5-Bromo-1,3-benzodioxole-4-carboxaldehyde (0.60 g, 2.62 mmol) was dissolved in acetone (25 mL) and slowly added to the permanganate solution and the reaction mixture was stirred at ambient temperature for 24 h at which time TLC analysis indicated the reaction complete. The reaction mixture was quenched with 5% sodium sulfite (100 mL). Concentrated HCl (10 mL) was added and the mixture turned a pale yellow color. The solution was extracted with ethyl acetate and the organic layers were dried with magnesium sulfate and concentrated by rotary evaporation to afford 0.34 g of product (1.39 mmol, 53% yield) as an off-white solid.

Workup

  1. customThe reaction mixture was quenched with 5% sodium sulfite (100 mL)
  2. additionConcentrated HCl (10 mL) was added
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialthe organic layers were dried with magnesium sulfate
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-797eeba805a44c77a5b7818b700d3777
Source dataset
uspto-grants-1999_09
Patent number
US05948817

Reaction notes

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