Toluene → Hexylnorbornene

HRID 1161625Notes

Reaction equation

HRID 1161625 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:7]1([CH3:13])[CH:12]=[CH:11]C=[CH:9][CH:8]=1.Cl[CH2:15]Cl>C1COCC1.C1(C)C=C(C)C=C(C)C=1>[CH2:2]([C:1]12[CH2:13][CH:7]([CH2:12][CH2:11]1)[CH:8]=[CH:9]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:15]

Participants

6

Reactant 3

HCID 1140TolueneHCID 6344DichloromethaneHCID 115971-Hexene

Product 1

HCID 21946566Hexylnorbornene

Reagents, catalysts & solvents 2

HCID 7947MesityleneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
8 °C

Procedure

HxNB, (10.0 g, 0.056 mol), 1-hexene (4.71 g, 0.056 mol) and toluene (56.7 g) were combined in a 250 mL serum bottle and heated to 8° C. in an oilbath form a solution. To this solution were added Pd1446, (4.10E-4 g, 2.80E-7 mol) and DAMABA, (2.20E-4 g, 2.80E-7 mol), each in the form of a concentrated solution in dichloromethane. After addition, the resulting mixture was maintained at 80° C. for 40 minutes. The homopolymer 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, 5.8 g was obtained (58%). The molecular weight of the copolymer, determined by GPC in THF solvent (polystyrene standard) provided Mw=121,541 and Mn=59,213. The refractive indices of this polymer were measured by prism coupling method and determined to be 1.5146 in TE mode and 1.5129 in TM mode at a wavelength of 633 nm. The Tg (eased on thermomechanical analysis (TMA) measurement) of this polymer was 208° C. The dried homopolymer was dissolved in sufficient mesitylene to result in a 10 wt % homopolymer solution.

Workup

  1. additionAfter addition
  2. temperaturethe resulting mixture was maintained at 80° C. for 40 minutes
  3. customThe homopolymer was precipitated
  4. additionby adding methanol
  5. customdrop wise into the vigorously stirred reaction mixture
  6. filtrationThe precipitated copolymer was collected by filtration
  7. customdried in an oven at 60° C. under vacuum
  8. customAfter drying
  9. custom5.8 g was obtained (58%)
  10. customprovided Mw=121,541 and Mn=59,213
  11. customwas 208° C
  12. customto result in a 10 wt % homopolymer solution

Sources & evidence

ORD record
ord-5c4b7da4246f4b62b7eac04c095714ea
Source dataset
uspto-grants-2010_10
Patent number
US07820356B2

Reaction notes

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