2,5-Di-tert-butylhydroquinone → 3a,4,7,7a-Tetrahydro-1H-4,7-methanoindene-1,3(2H)-dione

HRID 1415571

Reaktionsgleichung

Reaktionsgleichung von HRID 1415571
[C:1]1(=[O:7])[CH:5]=[CH:4][C:3](=[O:6])[CH2:2]1.[CH:8]1[CH2:12][CH:11]=[CH:10][CH:9]=1.C(C1C=C(O)C(C(C)(C)C)=CC=1O)(C)(C)C>C1C=CC=CC=1>[CH:10]12[CH2:11][CH:12]([CH:8]=[CH:9]1)[CH:4]1[CH:5]2[C:1](=[O:7])[CH2:2][C:3]1=[O:6]

Komponenten

5

Edukt 3

HCID 23742,5-Di-tert-butylhydroquinoneHCID 7612CyclopentadieneHCID 702582-Cyclopentene-1,4-dione

Produkt 1

HCID 135871813a,4,7,7a-Tetrahydro-1H-4,7-methanoindene-1,3(2H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 4-cyclopentene-1,3-dione (5 84g; 0.06 mole) in anhydrous benzene (20ml) was treated with freshly distilled cyclopentadiene (7.3g; 0.122 mole) together with a few crystals of 2,5-di-t-butyl hydroquinone. An immediate reaction ensued with concommitant crystallisation of the product. After standing at room temperature for 3 days the title compound was filtered and recrystallised from methanol, m.p. 183° C.

Aufarbeitung

  1. customAn immediate reaction
  2. customensued with concommitant crystallisation of the product
  3. filtrationthe title compound was filtered
  4. customrecrystallised from methanol, m.p. 183° C.

Quellen und Nachweise

ORD-Eintrag
ord-94edf95b6b2e4bf6a0e10601c5ca5b63
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04005219

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