Water → HCID 18183397, compound

HRID 2269590Notes

Reaction equation

HRID 2269590 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.[Br:13]([O-])(=O)=O.[K+].[OH2:18]>>[Br:13][C:12]1[CH:11]=[C:5]([C:6]([OH:7])=[O:18])[C:4]([C:9]([OH:8])=[O:10])=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 3

HCID 962WaterHCID 880694-Methylphthalic anhydrideHCID 23673461Potassium Bromate

Product 1

HCID 18183397HCID 18183397, compound

Conditions

Temperature
90 °C

Procedure

A suspension of 4-methylphthalic anhydride (1) (58.8 g, 0.363 mol) and potassium bromate (66.7 g, 0.400 mol) in 250 ml of water was heated to 90° C., and after the removal of the heating bath used, 250 ml of concentrated sulfuric acid was slowly added dropwise with vigorous stirring. After the completion of the dropping, the heating bath was attached again to heat the mixture at 90 to 100° C. for 3 hours with stirring. The mixture was then allowed to cool down to ambient temperature, and the precipitated solid was separated on a filter, and rinsed with cold water. The filtrate was extracted with three portions of ether. The combined organic phase was washed with successive water and saturated saline solution, and dried over anhydrous sodium sulfate. The ether solution was then concentrated to obtain a solid. The solid was combined with the solid separated previously on the filter were combined, and water was separated therefrom as a toluene azeotrope, to obtain a crude 5-bromo-4-methylphthalic acid (2).

Workup

  1. customafter the removal of the heating bath
  2. addition250 ml of concentrated sulfuric acid was slowly added dropwise with vigorous stirring
  3. temperatureto heat the mixture at 90 to 100° C. for 3 hours
  4. temperatureto cool down to ambient temperature
  5. customthe precipitated solid was separated on a filter
  6. washrinsed with cold water
  7. extractionThe filtrate was extracted with three portions of ether
  8. washThe combined organic phase was washed with successive water and saturated saline solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationThe ether solution was then concentrated
  11. customto obtain a solid
  12. customseparated previously on the filter
  13. customwater was separated

Sources & evidence

ORD record
ord-8b92120f529b4e2ba4da4e8dbc880d2f
Source dataset
uspto-grants-2001_12
Patent number
US06329494B1

Reaction notes

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