Thionyl Chloride → 4,9-Bis(propyloxy)naphtho[2,3-c]furan-1,3-dione

HRID 889481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889481
[CH2:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH2:16][CH2:17][CH3:18])=[C:7]([C:19]([OH:21])=[O:20])[C:6]=1[C:22]([OH:24])=O)[CH2:2][CH3:3].S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]1[C:6]2[C:22](=[O:24])[O:20][C:19](=[O:21])[C:7]=2[C:8]([O:15][CH2:16][CH2:17][CH3:18])=[C:9]2[C:14]=1[CH:13]=[CH:12][CH:11]=[CH:10]2)[CH2:2][CH3:3]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 210793301,4-Bis(propyloxy)-2,3-naphthalenedicarboxylic acid

Produkt 1

HCID 580176444,9-Bis(propyloxy)naphtho[2,3-c]furan-1,3-dioneAusbeute 103,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

1,4-Bis(propyloxy)-2,3-naphthalenedicarboxylic acid (8.91 g, 26.8 mmol) was suspended in chloroform (80 ml) and thionyl chloride (20.5 ml, 281.4 mmol) was added dropwise whilst monitoring the temperature (no significant change). The reaction was heated at 65° C. for 2.5 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The yellow/brown solid was azeotroped with chloroform (×3) to afford the title compound as a beige solid (8.74 g, 27.8 mmol).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe yellow/brown solid was azeotroped with chloroform (×3)

Quellen und Nachweise

ORD-Eintrag
ord-650bfd3b5b7540aaba914637203547b6
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252833B2

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