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

HRID 393499Notes

Reaction equation

HRID 393499 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 acidHCID 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 are dissolved in tetrahydrofuran or toluene. A radical reaction is 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 is 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.

Workup

  1. customA radical reaction
  2. customThe resin thus produced by this polymerization
  3. customis precipitated in ethyl ether
  4. dry with materialhexane and dried

Sources & evidence

ORD record
ord-a20214efb94441a39a7f941f21d504a9
Source dataset
uspto-grants-2004_10
Patent number
US06808859B1

Reaction notes

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