Azobisisobutyronitrile → Propyl maleimide t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate 2-hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

HRID 1975894Notes

Reaction equation

HRID 1975894 reaction equation
[CH2:1]([C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6])[CH2:2][CH3:3].[CH:11]12[CH2:18][CH2:17][CH:14]([CH:15]=[CH:16]1)[CH2:13][CH:12]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[CH:26]12[CH2:33][CH2:32][CH:29]([CH:30]=[CH:31]1)[CH2:28][CH:27]2[C:34]([O:36][CH2:37][CH2:38]CO)=[O:35].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[CH2:1]([C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6])[CH2:2][CH3:3].[CH:11]12[CH2:18][CH2:17][CH:14]([CH:15]=[CH:16]1)[CH2:13][CH:12]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[CH:26]12[CH2:33][CH2:32][CH:29]([CH:30]=[CH:31]1)[CH2:28][CH:27]2[C:34]([O:36][CH2:37][CH2:38][OH:6])=[O:35]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 18413667t-Butyl bicyclo[2,2,2]oct-5-ene-2-carboxylateHCID 21880478Propyl maleimideHCID 229870623-Hydroxypropyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

Product 1

HCID 86756652Propyl maleimide t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate 2-hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Propyl 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(propyl maleimide/t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate/2-hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylate) polymer was obtained at a yield of about 78%.

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 about 78%

Sources & evidence

ORD record
ord-4d0b982ccc8c4418a97df2eb09bec56b
Source dataset
uspto-grants-2001_05
Patent number
US06225020B1

Reaction notes

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