Dicyclopentadiene → 5-(3-Cyclohexen-1-yl)bicyclo(2.2.1)hept-2-ene

Dicyclopentadiene and 4-vinylcyclohexene in equimolar mixture were heated in an autoclave at 240° C. for 4-4.5 hours. The reaction product was diluted with cyclohexane and passed through a packed bed of alumina to remove the t-butylcatechol inhibitor introduced with the reactants. The resulting product mixture was distilled in a wiped film evaporator at 3 mm Hg pressure at 90° C. to produce a light fraction containing unreacted vinylcyclohexene and dicyclopentadiene and the mono-adducts of 4-vinylcyclohexene and cyclopentadiene. A 150 g sample of this distillate was vacuum distilled using a 10-tray Oldershaw column to give four fractions. The fourth fraction, 65 g, was shown by gas chromatographic analysis to consist of 0.15% dicyclopentadiene, 88.3% endo-5-(3-cyclohexen-1-yl)-2-norbornene, 6.1% exo-5-(3-cyclohexen-1-yl)-2-norbornene and two additional components present in the amount of 1.9% and 2.4% which are believed to be isomeric adducts of the formula ##STR5## several additional components totalling about 0.4%, 0.4% tricyclopentadiene and about 0.4% unidentified components. Analysis of the fraction by nuclear magnetic resonance indicated about 87 mole percent of the endo adduct, about 9 mole percent of the exo adduct and about 5% of the isomeric adducts.

1. customto remove the t-butylcatechol
2. additioninhibitor introduced with the reactants
3. distillationThe resulting product mixture was distilled in a wiped film evaporator at 3 mm Hg pressure at 90° C.
4. customto produce a light fraction
5. distillationdistilled
6. customto give four fractions

ORD-Eintrag

ord-3e4c7db8a0cf409bb5f189af3c19c842

Quelldatensatz

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05284929