Toluene → HCID 86613227, compound

HRID 909979Notes

Reaction equation

HRID 909979 reaction equation
[C:1]1([C:7]2[C:8]3([CH2:14][CH3:15])[CH2:13][CH:11]([CH:12]=2)[CH2:10][CH2:9]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]=[CH:17][CH2:18][CH2:19]CC.C1(C)C=CC=CC=1.ClCCl>C1COCC1.C1(C)C=C(C)C=C(C)C=1>[CH2:14]([C:8]12[CH2:13][CH:11]([CH2:10][CH2:9]1)[CH:12]=[CH:7]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH2:12]([C:11]12[CH2:13][CH:8]([CH2:9][CH2:10]1)[CH:14]=[CH:15]2)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 115971-HexeneHCID 86613229HCID 86613229, compound2×

Product 1

HCID 86613227HCID 86613227, compound

Reagents, catalysts & solvents 2

HCID 7947MesityleneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

HxNB (2.78 g, 0.0156 mol), Phenyl ethyl norbornene (PENB, CAS 29415-09-6) (7.22 g, 0.036 mol), 1-hexene (2.18 g, 0.026 mol) and toluene (57.0 g) were combined in a 250 mL serum bottle and heated to 120° C. in an oil bath. To this solution were added Pd1446 (3.0E-3 g, 2.1E-6 mol) and DANFABA (6.7E-3 g, 8.4E-6 mol) in concentrated solutions of dichloromethane. After addition, the resulting mixture was maintained at 120° C. for 1 hour. After cooling to room temperature, the copolymer was precipitated by adding methanol drop wise into the reaction mixture. The solid copolymer was collected by filtration and dried at 80° C. in a vacuum oven. The solid polymer was dissolved in an appropriate amount of mesitylene to give 10 wt % solid copolymer solution. After drying, 8.0 g was obtained (80%). The molecular weight of the polymer was determined by GPC methods in THF (poly(styrene) standard) Mw=127,332; Mn=39,206. The composition of the polymer was determined by 1H-NMR: HxNB/PENB=22/78. The composition of the copolymer was determined by 1H-NMR to be 54/46 HxNB/diPhNB. The refractive indices of this polymer were measured by prism coupling method and determined to be 1.5601 in TE mode and 1.5585 in TM mode at a wavelength of 633 nm. The dried copolymer was dissolved in sufficient mesitylene to result in a 10 wt % copolymer solution.

Workup

  1. additionAfter addition
  2. temperaturethe resulting mixture was maintained at 120° C. for 1 hour
  3. temperatureAfter cooling to room temperature
  4. customthe copolymer was precipitated
  5. additionby adding methanol
  6. filtrationThe solid copolymer was collected by filtration
  7. customdried at 80° C. in a vacuum oven
  8. dissolutionThe solid polymer was dissolved in an appropriate amount of mesitylene
  9. customto give 10 wt % solid copolymer solution
  10. customAfter drying
  11. custom8.0 g was obtained (80%)
  12. customto result in a 10 wt % copolymer solution

Sources & evidence

ORD record
ord-5d07b829d807453f9534874d92e31f5b
Source dataset
uspto-grants-2011_09
Patent number
US08021825B2

Reaction notes

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