Water → 5,8-Dihydro-1,4-naphthoquinone

HRID 36089

Reaktionsgleichung

Reaktionsgleichung von HRID 36089
[C:1]1(=[O:8])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[CH2:9]=[CH:10][CH:11]=[CH2:12].O>C1(C)C=CC=CC=1.C(O)(=O)C>[C:1]1(=[O:8])[C:6]2[CH2:12][CH:11]=[CH:10][CH2:9][C:5]=2[C:4](=[O:7])[CH:3]=[CH:2]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 4650QuinoneHCID 78451,3-Butadiene

Produkt 1

HCID 2238135,8-Dihydro-1,4-naphthoquinoneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

In toluene (30 ml) and acetic acid (10 ml), were dissolved 10.0 g (0.092 mol) of 1,4-benzoquinone, to which 10.0 g (0.18 mol) of 1,3-butadiene were added at -10° C. under stirring. Thereafter, the resultant mixture was gradually heated and stirred further for 3 hours at 40° C. The liquid reaction mixture was washed with water, and an organic layer was dried and concentrated under reduced pressure. Concentrated hydrochloric acid (1 ml) and ethanol (50 ml) were added to the residue, and the mixture was stirred for 1 hour at 40° C. After the liquid reaction mixture was concentrated under reduced pressure, the residue was dissolved in a liquid mixture of acetonitrile (100 ml) and water (30 ml). To the solution, were added 20.0 g (0.036 mol) of ceric ammonium nitrate at room temperature to stir the resultant mixture for 1 hour. The liquid reaction mixture was poured into water (200 ml) to make extraction with toluene (50 ml × 2). The resulting organic layer was washed with water, dried and concentrated under reduced pressure to obtain 13.3 g of a crude product of the title compound (yield: 91%).

Aufarbeitung

  1. stirringstirred further for 3 hours at 40° C
  2. customThe liquid reaction mixture
  3. washwas washed with water
  4. customan organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. additionConcentrated hydrochloric acid (1 ml) and ethanol (50 ml) were added to the residue
  7. stirringthe mixture was stirred for 1 hour at 40° C
  8. customAfter the liquid reaction mixture
  9. concentrationwas concentrated under reduced pressure
  10. dissolutionthe residue was dissolved in a liquid mixture of acetonitrile (100 ml) and water (30 ml)
  11. customThe liquid reaction mixture
  12. extractionextraction with toluene (50 ml × 2)
  13. washThe resulting organic layer was washed with water
  14. customdried
  15. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-977f78c9e987497bad643853aae1b4fe
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05412124

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