Methanol → HCID 131731368, compound

HRID 1019478Notes

Reaction equation

HRID 1019478 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]1([C:14]2[C:15]3([CH2:21][CH3:22])[CH2:20][CH:18]([CH:19]=2)[CH2:17][CH2:16]3)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(N=NC(C#N)(C)C)(C#N)C.[OH-].[Na+].CO>CCOC(C)=O.C1COCC1>[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH:2]=[CH:3]1.[C:8]1([C:14]2[C:15]3([CH2:21][CH3:22])[CH2:20][CH:18]([CH:19]=2)[CH2:17][CH2:16]3)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 14798Sodium HydroxideHCID 86613229HCID 86613229, compound

Product 1

HCID 131731368HCID 131731368, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Maleic Anhydride (MA, 14.7 g, 150 mmol), Phenyl Ethyl Norbornene (PENB, 29.7 g, 150 mmol) and AIBN (2.5 g, 15.0 mmol) was dissolved in EtOAc (27.1 g) and charged to a reaction vessel. The solution was sparged with nitrogen for 10 min to remove oxygen and then heated to 60° C. The mixture was allowed to stir at 60° C. for 24 hr. The reaction mixture was concentrated in vacuo and redissolved in THF (20 wt %). The resulting solution was added to the suspension of NaOH (6.6 g, 165 mmol), MeOH (24.0 g, 750 mmol) and THF (24.0 g) which were mixed at 70° C. for 1 hr. The mixture was allowed to stir for 3 hr at 70° C. and then was cooled to room temperature. The reaction mixture was treated with conc. HClaq for protonation, and then washed three times to remove residual salts and acid. The organic phase was separated and then concentrated in vacuo, redissolved in THF to form an approximately 20 wt % copolymer solution and then the copolymer was precipitated by adding the THF solution to hexane (20 fold excess). The copolymer was separated by filtration and dried in a vacuum oven at 80° C. for 16 hr. Approximately, 30.4 g (61%) of the Ring-opening polymer of MA/PENB with MeOH was isolated (GPC Mw=9,700 Mn=5,300).

Workup

  1. additioncharged to a reaction vessel
  2. customThe solution was sparged with nitrogen for 10 min
  3. customto remove oxygen
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutionredissolved in THF (20 wt %)
  6. additionwere mixed at 70° C. for 1 hr
  7. stirringto stir for 3 hr at 70° C.
  8. temperaturewas cooled to room temperature
  9. additionThe reaction mixture was treated with conc. HClaq for protonation
  10. washwashed three times
  11. customto remove residual salts and acid
  12. customThe organic phase was separated
  13. concentrationconcentrated in vacuo
  14. dissolutionredissolved in THF
  15. customto form an approximately 20 wt % copolymer solution
  16. customthe copolymer was precipitated
  17. additionby adding the THF solution to hexane (20 fold excess)
  18. customThe copolymer was separated by filtration
  19. customdried in a vacuum oven at 80° C. for 16 hr

Sources & evidence

ORD record
ord-a5d919d51abb42b7a91c2adee1bd516e
Source dataset
uspto-grants-2014_05
Patent number
US08715900B2

Reaction notes

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