Potassium Permanganate → 2,6-Dichloro-4-(2-methoxyethoxy)benzoic acid

HRID 1466226Notes

Reaction equation

HRID 1466226 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:7]=[C:6]([Cl:15])[C:3]=1[CH:4]=[O:5].[Mn]([O-])(=O)(=O)=[O:17].[K+]>CC(C)=O.O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:7]=[C:6]([Cl:15])[C:3]=1[C:4]([OH:17])=[O:5]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 866754202,6-Dichloro-4-(2-methoxyethoxy)benzaldehyde

Product 1

HCID 711500392,6-Dichloro-4-(2-methoxyethoxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2,6-Dichloro-4-(2-methoxyethoxy)benzaldehyde (0.5 g, 2.0 mmol) in acetone (20 mL) were cooled down in ice bath and then potassium permanganate (0.47 g, 3.0 mmol) in water (5 mL) was added slowly under vigorous stirring. The reaction mixture was warmed up slowly to room temperature and reacted over 24 h. The reaction mixture was filtered through celite and washed with acetone. The organic phase was evaporated and then re-dissolved in EtOAc to be extracted with 1N HCl aqueous solution. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuum to afford the compound 2,6-dichloro-4-(2-methoxyethoxy)benzoic acid.

Workup

  1. customreacted over 24 h
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with acetone
  4. customThe organic phase was evaporated
  5. dissolutionre-dissolved in EtOAc
  6. extractionto be extracted with 1N HCl aqueous solution
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-5ff4df5dc2a540d9b1995e05816e7abd
Source dataset
uspto-grants-2015_04
Patent number
US09000015B2

Reaction notes

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