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

HRID 507724

Reaktionsgleichung

Reaktionsgleichung von HRID 507724
[CH2:1]1[CH:5]2[C@@H:6]3C=C[C@H]([CH:4]2C=[CH:2]1)C3.[CH3:11][O:12][C:13](=[O:16])[CH:14]=[CH2:15].C1(C=CC(O)=CC=1)O>>[CH3:11][O:12][C:13]([CH:14]1[CH2:4][CH:5]2[CH2:6][CH:15]1[CH:2]=[CH:1]2)=[O:16]

Komponenten

4

Edukt 3

HCID 785HydroquinoneHCID 7294Methyl AcrylateHCID 15618652endo-Dicyclopentadiene

Produkt 1

HCID 250075Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylateAusbeute 85 %

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

DCPD (dicyclopentadiene, Aldrich, 256.5 mL, 1.9 mol), methylacrylate (Aldrich, 405 mL, 4.5 mol) and hydroquinone (3.2 g, 0.03 mol) were charged into a 2 L high-pressure autoclave, and the temperature was raised to 180° 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 50° C. (yield: 85%, exo/endo=41/59).

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-d52f6f21ef9144e3afed82d65bb496dc
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786231B2

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