Water → 4,5-Dimethoxyphthalic acid

HRID 1881207Notes

Reaction equation

HRID 1881207 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[O:7][CH2:6]2.[OH-:15].[Na+].[O-][Mn](=O)(=O)=O.[K+].[OH2:23]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]([OH:23])=[O:15])[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8]([OH:7])=[O:14]

Participants

5

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2304605,6-Dimethoxy-3H-isobenzofuran-1-oneHCID 516875Potassium Permanganate

Product 1

HCID 2909884,5-Dimethoxyphthalic acid

Procedure

To a mixture of 5,6-dimethoxy-3H-isobenzofuran-1-one (4.5 g) and 7% aqueous NaOH (47 ml) was added KMnO4 (4.0 g) diluted in water (125 ml). The mixture was stirred at room temperature for 4 days. Insoluble material was removed by filtration. The filtrate was cooled with ice-water bath and acidified with concentrated HCl. The acidic solution was extracted three times with ethyl acetate (300 ml). The combined organic layers were dried over anhydrous Na2SO4 and evaporated.

Workup

  1. customInsoluble material was removed by filtration
  2. temperatureThe filtrate was cooled with ice-water bath
  3. extractionThe acidic solution was extracted three times with ethyl acetate (300 ml)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-cb3ce5ebad0a4a1685bfee8cd89ad000
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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