Succinic anhydride → 2,5-Pyrrolidinedione, 1-[3-[3-(trimethoxysilyl)propoxy]phenyl]-

HRID 236631Notes

Reaction equation

HRID 236631 reaction equation
C1(=O)OC(=O)CC1.NC1C=C(O)C=CC=1.[C:16]1(=[O:29])[N:20]([C:21]2[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=2)[C:19](=[O:28])[CH2:18][CH2:17]1.[OH-].[Na+].Cl[CH2:33][CH2:34][CH2:35][Si:36]([O:41][CH3:42])([O:39][CH3:40])[O:37][CH3:38]>O.C1(C)C=CC=CC=1.CS(C)=O.C(O)(=O)C>[C:16]1(=[O:29])[N:20]([C:21]2[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=2)[O:27][CH2:33][CH2:34][CH2:35][Si:36]([O:41][CH3:42])([O:39][CH3:40])[O:37][CH3:38])[C:19](=[O:28])[CH2:18][CH2:17]1

Participants

10

Reactant 5

HCID 7922Succinic anhydrideHCID 115683-AminophenolHCID 14798Sodium HydroxideHCID 624493-(Trimethoxysilyl)propyl chlorideHCID 69513852,5-Pyrrolidinedione, 1-(3-hydroxyphenyl)-

Product 1

HCID 138791752,5-Pyrrolidinedione, 1-[3-[3-(trimethoxysilyl)propoxy]phenyl]-

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A solution containing 200 g of succinic anhydride, 218 g m-aminophenol and one liter of glacial acetic acid was heated at the boiling point for 16 hours in a reactor equipped with a mechanically driven stirrer and a water-cooled reflux condenser. The reaction mixture solidified upon cooling to ambient temperature. The solid was pulverized, washed with water to remove the acetic acid, then dried. The resultant m-succinimidophenol (105.1 g, 0.55 mole) together with 43.28 g of a 50% by weight aqueous solution of sodium hydroxide, 112 cc dimethylsulfoxide and 120 cc toluene were placed in a reactor equipped with a nitrogen inlet, water-cooled reflux condenser and Dean-Stark trap. The resultant mixture was heated to the boiling point for six hours under a nitrogen atmosphere to remove all of the water present by azeotropic distillation. The reaction mixture was then allowed to cool to about 75° C., at which time 109 g (0.56 mole) of 3-chloropropyl trimethoxysilane was added dropwise while the reaction mixture was stirred. Following completion of the addition the reaction mixture was heated at 115° C. for about 16 hours, following which the mixture was allowed to cool and was filtered to remove any solid material. The solvents were then removed under a pressure of about 15 mm of mercury at a temperature of about 60° C. The pressure was then reduced to 0.5 mm of mercury and the material boiling at 228° C. was collected. Analysis by vapor phase chromatography indicated that the purity of the product, a white solid, was greater than 98%. The infrared and nuclear magnetic resonance spectra of the product were consistent with the proposed structure.

Workup

  1. temperaturewas heated at the boiling point for 16 hours in a reactor
  2. customequipped with a mechanically driven stirrer
  3. temperaturereflux condenser
  4. washwashed with water
  5. customto remove the acetic acid
  6. customdried
  7. customequipped with a nitrogen inlet
  8. temperaturereflux condenser
  9. customto remove all of the water present
  10. distillationby azeotropic distillation
  11. additionwas added dropwise while the reaction mixture
  12. additioncompletion of the addition the reaction mixture
  13. temperaturewas heated at 115° C. for about 16 hours
  14. temperatureto cool
  15. filtrationwas filtered
  16. customto remove any solid material
  17. customThe solvents were then removed under a pressure of about 15 mm of mercury at a temperature of about 60° C
  18. customthe material boiling at 228° C. was collected

Sources & evidence

ORD record
ord-7d18265aa6944eafac999ce3c13daf37
Source dataset
uspto-grants-1987_02
Patent number
US04645844

Reaction notes

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