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

HRID 1835016Notes

Reaction equation

HRID 1835016 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH:15]12[CH2:21][CH:18]([CH:19]=[CH:20]1)[CH2:17][CH:16]2[C:22]([O:24][CH2:25][CH2:26][OH:27])=[O:23].[CH:28]12[CH2:34][CH:31]([CH:32]=[CH:33]1)[CH2:30][CH:29]2[C:35]([OH:37])=[O:36].[C:38]1(=[O:44])[O:43][C:41](=[O:42])[CH:40]=[CH:39]1.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1.O1CCCC1>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH:15]12[CH2:21][CH:18]([CH:19]=[CH:20]1)[CH2:17][CH:16]2[C:22]([O:24][CH2:25][CH2:26][OH:27])=[O:23].[CH:28]12[CH2:34][CH:31]([CH:32]=[CH:33]1)[CH2:30][CH:29]2[C:35]([OH:37])=[O:36].[C:41]1(=[O:42])[O:43][C:38](=[O:44])[CH:39]=[CH:40]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

To tetrahydrofuran or toluene was added 0.5 to 0.95 mole of tert-butyl 5-norbornene-2-carboxylate, 0.05 to 0.8 mole of 2-hydroxyethyl 5-norbornene-2-carboxylate, 0.01 to 0.2 mole of 5-norbornene-2-carboxylic acid, 0.5 to 1 mole of maleic anhydride and 0.5 to 10 g of 2,2′-azobisisobutyronitrile (AIBN).

Sources & evidence

ORD record
ord-1242273c413c47669351e37260db5353
Source dataset
uspto-grants-2004_08
Patent number
US06770414B2

Reaction notes

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