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

HRID 507725

Reaktionsgleichung

Reaktionsgleichung von HRID 507725
[CH2:1]1[CH:5]2[C@@H:6]3C=C[C@H]([CH:4]2C=[CH:2]1)C3.[CH2:11]([O:15][C:16](=[O:19])[CH:17]=[CH2:18])[CH2:12][CH2:13][CH3:14].C1(C=CC(O)=CC=1)O>>[CH2:11]([O:15][C:16]([CH:17]1[CH2:4][CH:5]2[CH2:6][CH:18]1[CH:2]=[CH:1]2)=[O:19])[CH2:12][CH2:13][CH3:14]

Komponenten

4

Edukt 3

HCID 785HydroquinoneHCID 8846Butyl AcrylateHCID 15618652endo-Dicyclopentadiene

Produkt 1

HCID 15608148Butyl bicyclo[2.2.1]hept-5-ene-2-carboxylateAusbeute 78 %

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

DCPD (dicyclopentadiene, Aldrich, 180 mL, 1.34 mol), butylacrylate (Junsei, 500 mL, 3.49 mol) and hydroquinone (2.7 g, 0.025 mol) were charged into a 2 L high-pressure autoclave, and the temperature was raised to 190° 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 under a reduced pressure (1 torr) using a vacuum pump to yield the title compound at 80° C. (yield: 78%, exo/endo=55/45).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-53a83014762d4b42abba2757068ede96
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786231B2

Verknüpfte Notizen

Wird geladen…