Dimethyl Sulfoxide → 2-n-Octyloxytetracene-5,12-dione

HRID 275073

Reaktionsgleichung

Reaktionsgleichung von HRID 275073
F[C:2]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:21])[C:4]=2[CH:3]=1.[CH2:22]([OH:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C1(C)C=CC=CC=1>[CH2:22]([O:30][C:2]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:21])[C:4]=2[CH:3]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 9571-OctanolHCID 11430Potassium CarbonateHCID 200898282-Fluorotetracene-5,12-dione

Produkt 1

HCID 200898292-n-Octyloxytetracene-5,12-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

20 g (72.4 mmol) of 2-fluoro-naphthacene-5,12-dione, 94.3 g of 1-octanol, 30.01 g (217.2 mmol) of anhydrous potassium carbonate and 200 ml of dimethyl sulfoxide (DMSO) are stirred at a bath temperature of 100° C. for 20 hours. The reaction mixture is cooled, toluene/dilute hydrochloric acid are added and the organic phase is separated off, washed twice with water, dried with sodium sulfate and evaporated. The residue is washed with pentane and recrystallized from cyclohexane. Yield: 22.9 g (82%), melting point 127°-129° C.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. customthe organic phase is separated off
  3. washwashed twice with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated
  6. washThe residue is washed with pentane
  7. customrecrystallized from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-ca3677ec7ca24c39a2ac893d571948c0
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391749

Verknüpfte Notizen

Wird geladen…