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N-Phenylmaleimide → 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-phenylpyrrolidine-2,5-dione

HRID 247614
Notes
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Reaction equation

HRID 247614 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]=1[OH:17])([CH3:6])([CH3:5])[CH3:4].[C:18]1([N:24]2[C:28](=[O:29])[CH:27]=[CH:26][C:25]2=[O:30])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[C:13]([C:9]1[CH:10]=[C:11]([CH:27]2[CH2:26][C:25](=[O:30])[N:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:28]2=[O:29])[CH:12]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:8]=1[OH:17])([CH3:16])([CH3:15])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 13662N-PhenylmaleimideHCID 24758Sodium hydrideHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 141483723-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-phenylpyrrolidine-2,5-dioneYield 2.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound is prepared by the procedure of Example 1 from 2.40 g (0.1 mol) of sodium hydride, 20.63 g (0.1 mol) of 2,6-di-tert-butylphenol, and 17.32 g (0.1 mol) of N-phenylmaleimide in tetrahydrofuran. The reaction mixture is concentrated in vacuo and the residue is dissolved in 150 ml of toluene. The toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (2×50 ml). The organic phase is dried over anhydrous sodium sulfate and then the solvent is removed in vacuo. The residue is triturated with petroleum ether to give 0.78 g (2%) of white crystals: mp 204° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in 150 ml of toluene
  3. extractionThe toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (2×50 ml)
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customThe residue is triturated with petroleum ether

Sources & evidence

ORD record
ord-c2d334ca504d491ba5ca09fb968575eb
Source dataset
uspto-grants-1987_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04709050

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes