Dicyclopentadiene → 5-(4-Benzocyclobutenyl)-2-norbornene

HRID 595612

Reaktionsgleichung

Reaktionsgleichung von HRID 595612
C([C:3]1[CH:10]=[CH:9][CH:8]=[C:5]2[CH2:6][CH2:7][C:4]=12)=C.C1[CH:15]2[CH:16]3[CH:20]=[CH:19][CH:18]([CH:14]2C=C1)[CH2:17]3.C(C1C=C(O)C(=CC=1)O)(C)(C)C>>[CH:6]1[C:5]2[CH:8]=[CH:9][C:10]([CH:20]3[CH2:19][CH:18]4[CH2:17][CH:16]3[CH:15]=[CH:14]4)=[CH:3][C:4]=2[CH:7]=1

Komponenten

4

Versuchsvorschrift

A 100-ml autoclave with an agitator was charge with 10 g (77 mmol) of 4-vinylbenzocyclobutene, 4.6 g (35 mmol) of dicyclopentadiene, and 438 mg (2.6 mmol) of 4-tert-butylcatechol and was then tightly closed. The reactants were allowed to react at 170° C. for two hours while stirring at 300 rpm. The product was then cooled and removed from the autoclave. The product was diluted with toluene, and the resulting polyvinylbenzocyclobutene was precipitated in methanol. Polyvinylbenzocyclobutene was filtered out, and the solvent was removed. The residue was transferred to a distillation apparatus. The residue was distilled under reduced pressure (127° C., 5 mmHg) to yield 3.0 g (15 mmol, yield 20%) of 5-(4-benzocyclobutenyl)-2-norbornene as a colorless and transparent liquid. 1H NMR structural identification showed that the present example produced a compound having the formula (2).

Aufarbeitung

  1. customwas then tightly closed
  2. customto react at 170° C. for two hours
  3. temperatureThe product was then cooled
  4. customremoved from the autoclave
  5. additionThe product was diluted with toluene
  6. customthe resulting polyvinylbenzocyclobutene was precipitated in methanol
  7. filtrationPolyvinylbenzocyclobutene was filtered out
  8. customthe solvent was removed
  9. distillationThe residue was distilled under reduced pressure (127° C., 5 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-c58c343648814098baf3e3341b3c4320
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243098B2

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