Azobisisobutyronitrile → 2-Hydroxyethyl 5-norbornene-2-carboxylate t-butyl 5-norbornene-2-carboxylate 5-norbornene 2-carboxylic acid maleic anhydride

HRID 366977Notes

Reaction equation

HRID 366977 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH:8]12[CH2:14][CH:11]([CH:12]=[CH:13]1)[CH2:10][CH:9]2[C:15]([O:17][CH2:18][CH2:19][OH:20])=[O:16].[CH:21]12[CH2:27][CH:24]([CH:25]=[CH:26]1)[CH2:23][CH:22]2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].[CH:35]12[CH2:41][CH:38]([CH:39]=[CH:40]1)[CH2:37][CH:36]2[C:42]([OH:44])=[O:43].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1.C1(C)C=CC=CC=1>[CH:8]12[CH2:14][CH:11]([CH:12]=[CH:13]1)[CH2:10][CH:9]2[C:15]([O:17][CH2:18][CH2:19][OH:20])=[O:16].[CH:21]12[CH2:27][CH:24]([CH:25]=[CH:26]1)[CH2:23][CH:22]2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].[CH:35]12[CH2:41][CH:38]([CH:39]=[CH:40]1)[CH2:37][CH:36]2[C:42]([OH:44])=[O:43].[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH:2]=[CH:3]1

Participants

8

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 789495-Norbornene-2-carboxylic acid2×HCID 120338232-Hydroxyethyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl ester

Product 1

HCID 865933172-Hydroxyethyl 5-norbornene-2-carboxylate t-butyl 5-norbornene-2-carboxylate 5-norbornene 2-carboxylic acid maleic anhydride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 mole of maleic anhydride, 0.05-0.8 moles of 2-hydroxyethyl 5-norbornene-2-carboxylate, 0.5-0.95 moles of t-butyl 5-norbornene-2-carboxylate and 0.01 to 0.2 moles of 5-norbornene 2-carboxylic acid (structures of which are shown in formula IX below) were dissolved in tetrahydrofuran or toluene. Thereafter, it was dissolved in a solvent. A radical reaction was executed at a temperature of about 60-70° C. for 4-24 hours under a nitrogen or argon atmosphere in the presence of 0.5-10 g of azobisisobutyronitrile (AIBN), as an initiator. The resin thus produced by this polymerization was precipitated in ethyl ether or hexane and dried to yield poly[2-hydroxyethyl 5-norbornene-2-carboxylate/t-butyl 5-norbornene-2-carboxylate/5-norbornene 2-carboxylic acid/maleic anhydride] resin of the following formula X. ##STR6##

Workup

  1. dissolutionThereafter, it was dissolved in a solvent
  2. customA radical reaction
  3. customThe resin thus produced by this polymerization
  4. customwas precipitated in ethyl ether
  5. dry with materialhexane and dried

Sources & evidence

ORD record
ord-07f8a455c9a24ac6a7c4122bf09575bb
Source dataset
uspto-grants-2000_10
Patent number
US06132926

Reaction notes

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