Tetrahydrofuran → HCID 86613231, compound

HRID 555214Notes

Reaction equation

HRID 555214 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2.[CH2:8]([O:12][CH3:13])[CH:9]1[O:11][CH2:10]1.[CH2:14]1[CH2:18]O[CH2:16][CH2:15]1>C1(C)C=CC=CC=1>[CH2:18]([C:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2)[CH2:14][CH2:15][CH3:16].[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2.[CH2:8]([O:12][CH3:13])[CH:9]1[O:11][CH2:10]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86613232HCID 86613232, compound

Product 1

HCID 86613231HCID 86613231, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent4×

Conditions

Temperature
80 °C

Procedure

BuNB (10.52 g, 0.07 mol), Methyl Glycidyl Ether Norbornene (AGENB, CAS 3188-75-8) (5.41 g, 0.03 mol), toluene (58.0 g) were added to a serum bottle in the drybox. The solution was stirred at 80° C. in an oil bath. To this solution were added a toluene solution (5 g) of (η6-toluene)Ni(C6F5)2 (0.69 g, 0.0014 mol). After the addition, the resulting mixture was maintained at room temperature for 4 hours. A toluene solution (87.0 g) was added to the reaction solution. 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, 12.74 g was obtained (80%). The molecular weight of the copolymer was determined by GPC in THF solvent (polystyrene standard) to be Mw=75,000 and Mn=30,000. The composition of the copolymer was determined by 1H-NMR to be (78/22) BuNB/AGENB copolymer. The refractive indices of this polymer were measured by prism coupling method and determined to be 1.5162 in TE mode and 1.5157 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. additionAfter the addition
  2. temperaturethe resulting mixture was maintained at room temperature for 4 hours
  3. customThe copolymer 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. custom12.74 g was obtained (80%)
  10. customto result in a 30 wt % copolymer solution

Sources & evidence

ORD record
ord-7b6df93af58e4080a7c706e7449af9b1
Source dataset
uspto-grants-2011_11
Patent number
US08053166B2

Reaction notes

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