p-Toluenesulfonic acid → N-(3-hydroxyphenyl)maleimide

HRID 728623Notes

Reaction equation

HRID 728623 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[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=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=C(C)C=1>[OH:15][C:11]1[CH:10]=[C:9]([N:8]2[C:1](=[O:7])[CH:2]=[CH:3][C:4]2=[O:6])[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7923Maleic AnhydrideHCID 115683-Aminophenol

Product 1

HCID 5325833N-(3-hydroxyphenyl)maleimide

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

A one-liter flask containing 52.8 grams (0.53 mole) of maleic anhydride dissolved in 200 ml of m-xylene was slowly charged with 55.0 grams (0.50 mole) of 3-aminophenol. The reaction temperature was maintained below 50° C. with cooling. Five grams of para-toluenesulfonic acid was then added to the flask and the reactor contents heated to reflux with a pot temperature of 148°-150° C. Water removal was complete after 8 hours of reflux under nitrogen with a Dean-Stark trap. The flask was cooled, xylene decanted, and the remaining product dried under reduced pressure. One hundred two grams of crude product containing N-(3-hydroxyphenyl) maleimide were recovered.

Workup

  1. temperatureThe reaction temperature was maintained below 50° C.
  2. temperaturewith cooling
  3. temperaturethe reactor contents heated
  4. temperatureto reflux with a pot temperature of 148°-150° C
  5. customWater removal
  6. temperatureof reflux under nitrogen with a Dean-Stark trap
  7. temperatureThe flask was cooled
  8. customxylene decanted
  9. customthe remaining product dried under reduced pressure
  10. additionOne hundred two grams of crude product containing N-(3-hydroxyphenyl) maleimide
  11. customwere recovered

Sources & evidence

ORD record
ord-f165aab68e9241aeaf3f4a142b3d4185
Source dataset
uspto-grants-1991_09
Patent number
US05049618

Reaction notes

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