1-Hexene → Decyl Norbornene Phenylethyl Norbornene

HRID 555213Notes

Reaction equation

HRID 555213 reaction equation
[CH2:1]([C:11]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C=CCCCC>ClCCl.C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([C:11]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:3]1([CH2:2][CH2:1][C:11]23[CH2:17][CH:14]([CH2:15][CH2:16]2)[CH:13]=[CH:12]3)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 115971-HexeneHCID 21922320Decyl Norbornene2×

Product 1

HCID 86613230Decyl Norbornene Phenylethyl Norbornene

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Decyl Norbornene (DeNB, CAS 22094-85-5) (6.84 g, 0.029 mol), PENB (23.16 g, 0.117 mol), 1-hexene (12.26 g, 0.146 mol) and toluene (170.0 g) were combined in a 500 mL serum bottle and heated to 80° C. in an oil bath to form a solution. To this solution were injected Pd1446 (0.0084 g, 5.84E-06 mol) and DANFABA (0.019 g, 2.33E-5 mol), each in the form of a concentrated solution in dichloromethane. After addition, the resulting mixture was maintained at 80° C. for 50 minutes. The copolymer was precipitated by adding methanol drop wise into the vigorously stirred reaction mixture. The precipitated copolymer was collected by filtration and dried in an oven at 60° C. under vacuum. After drying, 19.74 g was obtained (66%). The molecular weight of the copolymer was determined by GPC in THF solvent (polystyrene standard) to be Mw=78,000 and Mn=36,000. The composition of the copolymer was determined by 1H-NMR to be (19/81) DeNB/PENB copolymer. The refractive indices of this polymer were measured by prism coupling method and determined to be 1.5640 in TE mode and 1.5622 in TM mode at a wavelength of 633 nm. The dried copolymer was dissolved in sufficient toluene to result in a 30 wt % copolymer solution.

Workup

  1. customto form a solution
  2. additionAfter addition
  3. temperaturethe resulting mixture was maintained at 80° C. for 50 minutes
  4. customThe copolymer was precipitated
  5. additionby adding methanol
  6. customdrop wise into the vigorously stirred reaction mixture
  7. filtrationThe precipitated copolymer was collected by filtration
  8. customdried in an oven at 60° C. under vacuum
  9. customAfter drying
  10. custom19.74 g was obtained (66%)
  11. customto result in a 30 wt % copolymer solution

Sources & evidence

ORD record
ord-fec352489bfe4930918d768925fd1f61
Source dataset
uspto-grants-2011_11
Patent number
US08053166B2

Reaction notes

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