4-Aminophenol → 5,5'-[(1-Methylethylidene)bis(4,1-phenylenoxy)]bis[2-(4-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione]

HRID 1892073Notes

Reaction equation

HRID 1892073 reaction equation
[CH3:1][C:2]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]3[C:35](O[C:38](=[O:39])[C:31]=3[CH:30]=2)=[O:36])=[CH:24][CH:23]=1)([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]3[C:17](O[C:20](=[O:21])[C:13]=3[CH:12]=2)=[O:18])=[CH:6][CH:5]=1)[CH3:3].[NH2:40][C:41]1[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=1>CN(C=O)C>[CH3:3][C:2]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:30]=[C:31]3[C:32](=[CH:33][CH:34]=2)[C:35](=[O:36])[N:40]([C:41]2[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=2)[C:38]3=[O:39])=[CH:24][CH:23]=1)([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:14](=[CH:15][CH:16]=2)[C:17](=[O:18])[N:40]([C:41]2[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=2)[C:20]3=[O:21])=[CH:6][CH:5]=1)[CH3:1]

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 944832,2-Bis(4-(3,4-dicarboxyphenoxy)phenyl)propane dianhydride

Product 1

HCID 672382995,5'-[(1-Methylethylidene)bis(4,1-phenylenoxy)]bis[2-(4-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione]

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

247.2 g of 4,4′-(4,4′-isopropylidenediphenoxy)bis(phthalic anhydride) (0.47 mol) are dissolved in 200 ml of DMF in a 3 l three-necked flask with reflux divider, reflux condenser and distillation bridge. 105.8 g of 4-aminophenol (0.095 mol) are slowly added dropwise. The mixture is heated at reflux for 2 hours. Water is continuously removed by distillation during this process. The mixture is then cooled, diluted with 500 ml of dichloromethane, and washed twice with water. Finally, the product is washed with saturated NaCl solution. The organic phase is concentrated, and the residue is brought to the boil in 300 ml of methanol. After cooling, the residue is isolated by suction filtration and then washed with 200 ml of methanol.

Workup

  1. temperaturewith reflux divider
  2. temperaturereflux condenser
  3. distillationdistillation bridge
  4. temperatureThe mixture is heated
  5. temperatureat reflux for 2 hours
  6. customWater is continuously removed by distillation during this process
  7. temperatureThe mixture is then cooled
  8. additiondiluted with 500 ml of dichloromethane
  9. washwashed twice with water
  10. washFinally, the product is washed with saturated NaCl solution
  11. concentrationThe organic phase is concentrated
  12. temperatureAfter cooling
  13. customthe residue is isolated by suction filtration
  14. washwashed with 200 ml of methanol

Sources & evidence

ORD record
ord-acdb6b4a0bfe4f0eaa617473d0b03efa
Source dataset
uspto-grants-2013_08
Patent number
US08507635B2

Reaction notes

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