Acetic Acid → 1,2-Phenanthrenedione

HRID 382922

Reaktionsgleichung

Reaktionsgleichung von HRID 382922
[CH:1]1[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=CC=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:15]([OH:18])(=O)[CH3:16].Br([O-])(=O)=[O:20].[K+].BrBr>O>[C:15]1(=[O:18])[C:16]2[CH:8]=[CH:7][C:6]3[C:5](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=[CH:2][C:1]1=[O:20]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 995PhenanthreneHCID 24408BromineHCID 23673461Potassium Bromate

Produkt 1

HCID 30805661,2-PhenanthrenedioneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
72.5 °C

Versuchsvorschrift

Phenanthrene (16 g, Aldrich Tech Grade (90 percent), 0.081 mol) and acetic acid (200 ml) were stirred and heated to 70-75° C. Potassium bromate (32 g, 0.19 mol) was added in 2 portions. After the addition of the first portion the temperature rose to reflux with evolution of bromine vapors. The second portion was added and the condenser was replaced by a distillation head. The heating was continued until the distillate was colorless. The deep red solution was cooled and poured into water (300 ml) and the precipitate was isolated by filtration. The crude product was purified by reslurrying in 100 ml of hot (70° C.) aqueous sodium bisulfite solution (40 percent) and filtering while hot. The deep red filtrate was cooled and treated with aqueous sodium carbonate until basic. The precipitated product was recovered by extraction with methylene chloride, dried and concentrated to yield 13.4 g (80 percent yield) of orange yellow solid: mp 182-184° C.

Aufarbeitung

  1. additionAfter the addition of the first portion the temperature
  2. additionThe second portion was added
  3. temperatureThe deep red solution was cooled
  4. customthe precipitate was isolated by filtration
  5. customThe crude product was purified
  6. customby reslurrying in 100 ml of hot (70° C.) aqueous sodium bisulfite solution (40 percent)
  7. filtrationfiltering while hot
  8. temperatureThe deep red filtrate was cooled
  9. additiontreated with aqueous sodium carbonate until basic
  10. customThe precipitated product was recovered by extraction with methylene chloride
  11. customdried
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f340790ec03b4833bd68969d8dffd5ca
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310256B1

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