Azobisisobutyronitrile → Maleic anhydride t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate 3-hydroxypropyl 5-norbornene-2-carboxylate

HRID 429011Notes

Reaction equation

HRID 429011 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH:8]12[CH2:15][CH2:14][CH:11]([CH:12]=[CH:13]1)[CH2:10][CH:9]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH:2]=[CH:3]1.[CH:8]12[CH2:15][CH2:14][CH:11]([CH:12]=[CH:13]1)[CH2:10][CH:9]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[CH:8]12[CH2:13][CH:11]([CH:14]=[CH:15]1)[CH2:10][CH:9]2[C:16]([O:18][CH2:19][CH2:22][CH2:4][OH:5])=[O:17]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 18413667t-Butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

Product 1

HCID 86757578Maleic anhydride t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate 3-hydroxypropyl 5-norbornene-2-carboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Maleic anhydride (1 mol.), t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate (0.5 mol.), and 3-hydroxy propyl 5-norbornene-2-carboxylate (0.5 mol.) were dissolved in 200 gms of tetrahydrofuran (THF), 6 gms of 2,2′-azobisisobutyronitrile (AIBN) was added thereto, and then the resultant solution was reacted at a temperature of 67° C. in a nitrogen atmosphere for 10 hours. After a high molecule weight was achieved by the reaction, the resultant product was precipitated in an ethyl ether solvent. The gathered precipitate was dried, and 150 gms of the desirable poly(maleic anhydride/t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate/3-hydroxypropyl 5-norbornene-2-carboxylate) polymer was obtained at a yield of about 50%. NMR spectra of the polymer is illustrated in FIG. 5.

Workup

  1. customAfter a high molecule weight was achieved by the reaction
  2. customthe resultant product was precipitated in an ethyl ether solvent
  3. customThe gathered precipitate was dried

Sources & evidence

ORD record
ord-cf7fa89251d3477eb64d7e31765bd6fd
Source dataset
uspto-grants-2001_11
Patent number
US06316162B1

Reaction notes

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