Hydroquinone → Benzyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

HRID 507731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507731
[CH2:1]1[CH:5]2[C@@H:6]3C=C[C@H]([CH:4]2C=[CH:2]1)C3.[C:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:14])[CH:12]=[CH2:13].C1(C=CC(O)=CC=1)O>>[CH2:16]([O:15][C:11]([CH:12]1[CH2:4][CH:5]2[CH2:6][CH:13]1[CH:2]=[CH:1]2)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

4

Edukt 3

HCID 785HydroquinoneHCID 75617Benzyl acrylateHCID 15618652endo-Dicyclopentadiene

Produkt 1

HCID 4083792Benzyl bicyclo[2.2.1]hept-5-ene-2-carboxylateAusbeute 65 %

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

DCPD (dicyclopentadiene, Aldrich, 67.32 ml, 0.5 mol), benzyl acrylate (Lancaster, 163 g, 1.0 mol) and hydroquinone (0.23 g, 2.1 mmol) were charged into a 2 L high-pressure autoclave, and the temperature was raised to 200° C. The resulting mixture was reacted for 5 hours with stirring at 300 rpm. After the reaction was completed, the reaction mixture was cooled and transferred to a distilling apparatus. The reaction mixture was distilled twice under a reduced pressure (1 torr) using a vacuum pump to yield the title compound at 190° C. (yield: 65%, exo/endo=56/44).

Aufarbeitung

  1. customThe resulting mixture was reacted for 5 hours
  2. temperaturethe reaction mixture was cooled
  3. distillationThe reaction mixture was distilled twice under a reduced pressure (1 torr)

Quellen und Nachweise

ORD-Eintrag
ord-ef91630c3186427586802be853997ccc
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786230B2

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