Azobisisobutyronitrile → cis-5-Norbornene-endo-2,3-dicarboxylic Anhydride tert-butyl 5-Norbornene-2-carboxylate maleic Anhydride mono-methyl cis-5-Norbornene-endo-2,3-dicarboxylate 5-norbornene-2-carboxylic Acid

HRID 1611420Notes

Reaction equation

HRID 1611420 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]1[C@@H:12]2[CH:13]3[C:18](=[O:19])[O:17][C:15](=[O:16])[CH:14]3[C@H:9]1[CH:10]=[CH:11]2.[CH3:20][O:21][C:22]([CH:24]1[CH:28]([C:29]([OH:31])=[O:30])[CH:27]2[CH:32]=[CH:33][CH:25]1[CH2:26]2)=[O:23].[C:34]([O:38][C:39]([CH:41]1[CH2:46][CH:45]2[CH2:47][CH:42]1[CH:43]=[CH:44]2)=[O:40])([CH3:37])([CH3:36])[CH3:35].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[CH2:8]1[C@@H:12]2[CH:13]3[C:18](=[O:19])[O:17][C:15](=[O:16])[CH:14]3[C@H:9]1[CH:10]=[CH:11]2.[CH:42]12[CH2:47][CH:45]([CH:44]=[CH:43]1)[CH2:46][CH:41]2[C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40].[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH:2]=[CH:3]1.[CH3:20][O:21][C:22]([CH:24]1[CH:28]([C:29]([OH:31])=[O:30])[CH:27]2[CH:32]=[CH:33][CH:25]1[CH2:26]2)=[O:23].[CH:9]12[CH2:8][CH:12]([CH:11]=[CH:10]1)[CH2:13][CH:14]2[C:15]([OH:17])=[O:16]

Participants

7

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 984652-Methyl bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylateHCID 9964188cis-5-Norbornene-endo-2,3-dicarboxylic anhydrideHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl ester

Product 1

HCID 131723902cis-5-Norbornene-endo-2,3-dicarboxylic Anhydride tert-butyl 5-Norbornene-2-carboxylate maleic Anhydride mono-methyl cis-5-Norbornene-endo-2,3-dicarboxylate 5-norbornene-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Maleic anhydride (1.0 mole), cis-5-norbornene-endo-2,3-dicarboxylic anhydride (0.2 mole), mono-methyl cis-5-norbornene-endo-2,3-dicarboxylate (0.15 mole) and tert-butyl-5-norbornene-2-carboxylate (0.65 mole) are dissolved in tetrahydrofuran. Then, 0.5 to 10 g of AIBN (azobisisobutyronitrile) as a polymerization initiator is added thereto, and the resultant mixture is reacted at about 60-70° C. for 4 to 24 hours under nitrogen or argon atmosphere. The polymer thus obtained is precipitated from ethyl ether or hexane, and dried to obtain the compound represented by the following Chemical Formula 101.

Workup

  1. customThe polymer thus obtained
  2. customis precipitated from ethyl ether or hexane
  3. customdried
  4. customto obtain the compound

Sources & evidence

ORD record
ord-c1bc7c4a979845838d0d71f4f84a1cf1
Source dataset
uspto-grants-2006_01
Patent number
US06987155B2

Reaction notes

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