Maleic Anhydride → 28122-54-5

HRID 363055Notes

Reaction equation

HRID 363055 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1>C1(C)C(C)=CC=CC=1>[OH:15][C:11]1[CH:10]=[C:9]([NH:8][C:4](=[O:5])/[CH:3]=[CH:2]\[C:1]([OH:6])=[O:7])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7923Maleic Anhydride2×HCID 115683-Aminophenol

Product 1

HCID 155090128122-54-5

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
50 °C

Procedure

A dry 3-liter 3-neck round bottom flask was fitted with a stirrer and thermocouple arrangement. The system was flushed with nitrogen and charged with 211 grams (2.15 moles) of maleic anhydride dissolved in 800 ml of xylene. The maleic anhydride was heated with stirring at 50° C. to form a solution. 3-aminophenol (220 g, 2.02 moles) was then slowly added neat to the solution with vigorous stirring over a period of about 5 minutes. The flask was again flushed with nitrogen and sealed under a nitrogen balloon. The flask was held at 50°-55° C. with vigorous stirring for 4 hours. At the end of 4 hours, the stirring was continued and the flask and contents were cooled with tap water/wet ice to 10° C. The bright yellow-colored slurry was readily poured out of the neck of the flask and vacuum filtered through a No. 4 filter paper to give a wet filter cake. The product was dried at a temperature below 50° C. in a draft hood. The yellow product was a powder melting at 115° C. Specific gravity was 1.210.

Workup

  1. customA dry 3-liter 3-neck round bottom flask was fitted with a stirrer
  2. customThe system was flushed with nitrogen
  3. customto form a solution
  4. stirringslowly added neat to the solution with vigorous stirring over a period of about 5 minutes
  5. customThe flask was again flushed with nitrogen
  6. customsealed under a nitrogen balloon
  7. customwas held at 50°-55° C.
  8. stirringwith vigorous stirring for 4 hours
  9. customAt the end of 4 hours
  10. temperaturethe flask and contents were cooled with tap water/wet ice to 10° C
  11. additionThe bright yellow-colored slurry was readily poured out of the neck of the flask and vacuum
  12. filtrationfiltered through a No
  13. filtration4 filter paper
  14. customto give a wet filter cake
  15. customThe product was dried at a temperature below 50° C. in a draft hood

Sources & evidence

ORD record
ord-dde444122207404a9a3a8075ef45e7b4
Source dataset
uspto-grants-1999_02
Patent number
US05872167

Reaction notes

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