Maleic Anhydride → 2-Hydroxyethyl oxabicyclo[2,2,1]hept-5-ene-2-carboxylate t-butyl 5-norbornene-2-carboxylate 5-norbornene-2,3-dicarboxylic acid maleic anhydride

HRID 2228364

Reaction equation

HRID 2228364 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[O:3][CH:2]2[C:8]([O:10][CH2:11][CH2:12][OH:13])=[O:9].[CH:14]12[CH2:20][CH:17]([CH:18]=[CH:19]1)[CH2:16][CH:15]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[CH:28]12[CH2:34][CH:31]([CH:32]=[CH:33]1)[CH:30]([C:35]([OH:37])=[O:36])[CH:29]2[C:38]([OH:40])=[O:39].[C:41]1(=[O:47])[O:46][C:44](=[O:45])[CH:43]=[CH:42]1>O1CCCC1>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[O:3][CH:2]2[C:8]([O:10][CH2:11][CH2:12][OH:13])=[O:9].[CH:14]12[CH2:20][CH:17]([CH:18]=[CH:19]1)[CH2:16][CH:15]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[CH:28]12[CH2:34][CH:31]([CH:32]=[CH:33]1)[CH:30]([C:35]([OH:37])=[O:36])[CH:29]2[C:38]([OH:40])=[O:39].[C:44]1(=[O:45])[O:46][C:41](=[O:47])[CH:42]=[CH:43]1

Participants

6

Reactant 4

HCID 7923Maleic AnhydrideHCID 979655-Norbornene-2,3-dicarboxylic acidHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterHCID 701791922-Hydroxyethyl oxabicyclo[2,2,1]hept-5-ene-2-carboxylate

Product 1

HCID 867583192-Hydroxyethyl oxabicyclo[2,2,1]hept-5-ene-2-carboxylate t-butyl 5-norbornene-2-carboxylate 5-norbornene-2,3-dicarboxylic acid maleic anhydrideYield 266.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-hydroxyethyl oxabicyclo[2,2,1]hept-5-ene-2-carboxylate (0.1 mol), t-butyl 5-norbornene-2-carboxylate (0.85 mol), 5-norbornene-2,3-dicarboxylic acid (0.05 mol) and maleic anhydride (1 mol) were dissolved in a tetrahydrofuran solvent (200 g). 2,2-azobisisobutyonitrile (5.84 g) was added, and the solution was mixed. The solution was polymerized at a temperature of 67° C. in a nitrogen atmosphere for 10 hours. After the polymerization reaction was completed, the polymer was precipitated in an ethyl ether solvent, then dried in a vacuum to obtain the pure title polymer (87.627 g). (yield: 30%, purity: 99.9%).

Workup

  1. additionthe solution was mixed
  2. customThe solution was polymerized at a temperature of 67° C. in a nitrogen atmosphere for 10 hours
  3. customAfter the polymerization reaction
  4. customthe polymer was precipitated in an ethyl ether solvent
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-116f96f2f9944ac6813a6f6f2777554f
Source dataset
uspto-grants-2002_07
Patent number
US06416926B1

Linked notes

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