Toluene → 5,6-Dihydrodicyclopentadiene Ethylene

HRID 1028326Notes

Reaction equation

HRID 1028326 reaction equation
[CH2:1]1[CH:5]2[CH:6]3[CH2:10][CH:9]=[CH:8][CH:7]3[CH:3]([CH2:4]2)[CH2:2]1.[C:11]1(C)C=CC=C[CH:12]=1.C([Al](CC(C)C)CC(C)C)C(C)C.C=C>CO>[CH2:2]1[CH:3]2[CH:7]3[CH2:8][CH:9]=[CH:10][CH:6]3[CH:5]([CH2:4]2)[CH2:1]1.[CH2:11]=[CH2:12]

Participants

6

Conditions

Temperature
70 °C

Procedure

5,6-dihydrodicyclopentadiene (5.37 g, 40 mmol) and magnetic bars were added into a polymerization reactor in a nitrogen atmosphere, after which toluene was added thereto so as to obtain a total amount of 28 ml. This polymerization reactor was heated to 70° C. with stirring. A compound (0.7 mg, 2 μmol) represented by Formula 6, [Ph3C]+[B(C6F5)4]− (7.4 mg, 8.0 μmol), and triisobutylaluminum (160 mg, 800 μmol) were mixed with 2.0 ml of toluene in a dry box, after which the resulting mixture was added into the reactor using a syringe while being stirred at 70° C., and also ethylene gas was fed therein at a pressure of 60 psig. After 3 min, the ethylene pressure was released, and the reactor was opened and thus the reaction solution was introduced into a vessel containing 30 ml of methanol and thus the reaction product precipitated. Filtration was performed, thus obtaining a precipitate. The precipitate was decompressed to a vacuum at 100° C., so that the remaining solvent was removed therefrom, thereby obtaining 1.8 g of a polymer material.

Workup

  1. customso as to obtain a total amount of 28 ml
  2. additionafter which the resulting mixture was added into the reactor
  3. stirringwhile being stirred at 70° C.
  4. additionthus the reaction solution was introduced into a vessel
  5. customthus the reaction product precipitated
  6. filtrationFiltration
  7. customthus obtaining a precipitate
  8. customwas decompressed to a vacuum at 100° C., so that the remaining solvent
  9. customwas removed

Sources & evidence

ORD record
ord-653d1396bdf14b3285532aa112eee761
Source dataset
uspto-grants-2014_05
Patent number
US08735521B2

Reaction notes

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