1-Butanol → HCID 131731368, compound

HRID 1019475Notes

Reaction equation

HRID 1019475 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>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

7

Reactant 5

HCID 2631-ButanolHCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 14798Sodium HydroxideHCID 86613229HCID 86613229, compound

Product 1

HCID 131731368HCID 131731368, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 THF (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 23 hr, after which the solution was diluted to 20 wt % with 181.3 g of THF. The resulting solution was added to the suspension of NaOH (8.8 g, 220 mmol), BuOH (74.0 g, 1 mol) and THF (80.0 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 cone. 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, 44.4 g (75%) of the ROMA copolymer of MA/PENB with BuOH was isolated (GPC Mw=7,700 Mn=4,000).

Workup

  1. additioncharged to an appropriately sized reaction vessel
  2. customThe solution was sparged with nitrogen for 10 min
  3. customto remove oxygen
  4. additionafter which the solution was diluted to 20 wt % with 181.3 g of THF
  5. additionwere mixed at 70° C. for 1 hr
  6. stirringto stir for 2 hr at 70° C.
  7. temperaturewas cooled to room temperature
  8. additionThe reaction mixture was treated with cone
  9. washHClaq for protonation, and then washed three times
  10. customto remove residual salts and acid
  11. customThe organic phase was separated
  12. concentrationconcentrated in vacuo
  13. dissolutionredissolved in THF
  14. customto form an approximately 20 wt % copolymer solution
  15. customthe copolymer was precipitated
  16. additionby adding the THF solution to hexane (20 fold excess)
  17. customThe copolymer was separated by filtration
  18. customdried in a vacuum oven at 80° C. for 16 hr

Sources & evidence

ORD record
ord-ea3f6c2c23104378aaa9f357bc1df208
Source dataset
uspto-grants-2014_05
Patent number
US08715900B2

Reaction notes

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