1-(4-hydroxyphenyl)-1H-pyrrole-2,5-dione → 3-methoxy-4-(1-ethoxyethoxy)styrene N-(4-hydroxyphenyl)maleimide

HRID 2217947Notes

Reaction equation

HRID 2217947 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[CH:6]=[CH2:7].[OH:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:28](=[O:29])[CH:27]=[CH:26][C:25]2=[O:30])=[CH:20][CH:19]=1>O1CCCC1.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[CH:6]=[CH2:7].[OH:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:25](=[O:30])[CH:26]=[CH:27][C:28]2=[O:29])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 817341-(4-hydroxyphenyl)-1H-pyrrole-2,5-dioneHCID 23084984HCID 23084984, compound

Product 1

HCID 866040693-methoxy-4-(1-ethoxyethoxy)styrene N-(4-hydroxyphenyl)maleimideYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Conditions

Temperature
65 °C

Procedure

In a reaction vessel, 111.14 g (0.5 mol) of 3-methoxy-4-(1-ethoxyethoxy)styrene and 94.59 g (0.5 mol) of N-(4-hydroxyphenyl)maleimide were dissolved in 400 ml of tetrahydrofuran. While stirring the resulting solution, a nitrogen gas was passed into the system. Subsequently, 12.42 g (0.05 mol) of polymerization initiator V-65 (produced by Wako Pure Chemical Industries, Ltd.) was added thereto and the reaction solution was heated at 65° C. After stirring under heat for 10 hours by adding V-65 in the same amount as above every one hour, the reaction solution was allowed to cool to room temperature and then added dropwise in 5 L of hexane to precipitate a polymer. The solid obtained by filtration was dissolved in 800 ml of tetrahydrofuran and the resulting solution was again added dropwise in 5 L of hexane. After filtration, the solid obtained was dried under reduced pressure to obtain 181.04 g of a 3-methoxy-4-(1-ethoxyethoxy)styrene/N-(4-hydroxyphenyl)maleimide copolymer.

Workup

  1. customSubsequently, 12.42 g (0.05 mol) of polymerization initiator
  2. custom(produced by Wako Pure Chemical Industries, Ltd.)
  3. additionwas added
  4. stirringAfter stirring
  5. temperatureunder heat for 10 hours
  6. additionby adding V-65 in the same amount as above every one hour
  7. temperatureto cool to room temperature
  8. customto precipitate a polymer
  9. customThe solid obtained by filtration
  10. filtrationAfter filtration
  11. customthe solid obtained
  12. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-2d9eae9bd16f4795b56e953c5ba9ef37
Source dataset
uspto-grants-2008_08
Patent number
US07410747B2

Reaction notes

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