Ethanol → 4,5-Dimethoxyphthalic acid

HRID 2111615Notes

Reaction equation

HRID 2111615 reaction equation
[OH-:1].[Na+].[CH3:3][O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1C[O:8][C:9]2=[O:10].[Mn]([O-])(=O)(=O)=O.[K+].[CH2:23]([OH:25])C>>[CH3:16][O:15][C:14]1[CH:13]=[C:12]([C:23]([OH:25])=[O:1])[C:11](=[CH:6][C:5]=1[O:4][CH3:3])[C:9]([OH:8])=[O:10]

Participants

5

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 126376234,5-Dimethoxy-2-benzofuran-1(3H)-one

Product 1

HCID 2909884,5-Dimethoxyphthalic acid

Conditions

Temperature
25 °C

Procedure

An aqueous 2N sodium hydroxide solution of the product of above-mentioned (a) (3.0 g, 15 mmol) was added dropwise with stirring to a 6% aqueous solution of potassium permanganate (50 ml) under ice cooling, and the reaction solution was stirred overnight with gradually raising the temperature to 25° C. To the reaction solution was added ethanol and the precipitated manganese dioxide was filtered off. The filtrate was acidified with concentrated hydrochloric acid and concentrated under reduced pressure. To the residue was added methanol and stirred for 10 minutes. After the insoluble materials were filtered off, the filtrate was concentrated under reduced pressure to give 4.1 g of 4,5-dimethoxyphthalic acid.

Workup

  1. filtrationthe precipitated manganese dioxide was filtered off
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added methanol
  4. stirringstirred for 10 minutes
  5. filtrationAfter the insoluble materials were filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49393fb281c54496b9c26fbcfa99448a
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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