1-Butanol → HCID 131731368, compound

HRID 2204938Notes

Reaction equation

HRID 2204938 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+].C(O)CCC>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 2631-ButanolHCID 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, 19.6 g, 200.0 mmol), Phenyl Ethyl Norbornene (PENB, 39.6 g, 200 mmol) and AIBN (3.3 g, 20.0 mmol) was dissolved in EtOAc (36.2 g) and charged to an appropriately sized 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 20 hr. The reaction mixture was concentrated in vacuo and redissolved in THF (20 wt. %). The resulting solution was added to the suspension of NaOH (8.80 g, 220 mmol), BuOH (74.12 g, 1 mol) and THF (74.12 g) which were mixed at 70° C. for 1 hr. The mixture was allowed to stir for 2 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, 37.5 g (51%) of the ROMA copolymer of MA/PENB with BuOH was isolated (GPC Mw=9,900 Mn=5,400).

Workup

  1. additioncharged to an appropriately sized 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 2 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-9860cfc8229749eaa502fb2095c98511
Source dataset
uspto-grants-2016_06
Patent number
US09366956B2

Reaction notes

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