Azobisisobutyronitrile → Ethyl maleimide t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate 3-hydroxypropyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

HRID 1975895Notes

Reaction equation

HRID 1975895 reaction equation
[CH2:1]([C:3]1[C:4]([NH:6][C:7](=[O:9])[CH:8]=1)=[O:5])[CH3:2].[CH:10]12[CH2:17][CH2:16][CH:13]([CH:14]=[CH:15]1)[CH2:12][CH:11]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[CH:25]12[CH2:32][CH2:31][CH:28]([CH:29]=[CH:30]1)[CH2:27][CH:26]2[C:33]([O:35][CH2:36][CH2:37][CH2:38][OH:39])=[O:34].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[CH2:1]([C:3]1[C:4]([NH:6][C:7](=[O:9])[CH:8]=1)=[O:5])[CH3:2].[CH:10]12[CH2:17][CH2:16][CH:13]([CH:14]=[CH:15]1)[CH2:12][CH:11]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[CH:25]12[CH2:32][CH2:31][CH:28]([CH:29]=[CH:30]1)[CH2:27][CH:26]2[C:33]([O:35][CH2:36][CH2:37][CH2:38][OH:39])=[O:34]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 14671028Ethyl maleimideHCID 18413667t-Butyl bicyclo[2,2,2]oct-5-ene-2-carboxylateHCID 229870623-Hydroxypropyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

Product 1

HCID 131722531Ethyl maleimide t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate 3-hydroxypropyl bicyclo[2,2,2]oct-5-ene-2-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl maleimide (1 mol.), t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate (0.5 mol.) and 3-hydroxypropyl bicyclo[2,2,2]oct-5-ene-2-carboxylate (0.5 mol) were dissolved in 50 g to 300 g of tetrahydrofuran (THF), 2 g to 15 g of 2,2′-azobisisobutyronitrile (AIBN) was added thereto, and the resulting solution was reacted at a temperature between 60° C. and 70° C. in a nitrogen atmosphere for 10 hours. After a high molecular weight was achieved by the reaction, the resultant product was precipitated in an ethyl ether or hexane solvent. The gathered precipitate was dried, and the desired poly(ethyl maleimide/t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate/bicyclo[2,2,2]oct-5-ene-2-carboxylate) polymer was obtained at a yield of 75%

Workup

  1. customthe resulting solution was reacted at a temperature between 60° C. and 70° C. in a nitrogen atmosphere for 10 hours
  2. customAfter a high molecular weight was achieved by the reaction
  3. customthe resultant product was precipitated in an ethyl ether or hexane solvent
  4. customThe gathered precipitate was dried
  5. customwas obtained at a yield of 75%

Sources & evidence

ORD record
ord-562ac457a4964c3aac994e6d27e8b4d6
Source dataset
uspto-grants-2001_05
Patent number
US06225020B1

Reaction notes

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