1,4-Naphthalenediol → 5,14-Pentacenedione

HRID 1644008

Reaktionsgleichung

Reaktionsgleichung von HRID 1644008
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[O:12])[C:2]=1[CH:13]=[O:14].O[C:16]1[C:25]2[C:20](=CC=CC=2)[C:19](O)=[CH:18][CH:17]=1>>[CH:16]1[C:25]2[C:13](=[O:14])[C:2]3[C:3](=[CH:4][C:5]4[C:10]([CH:1]=3)=[CH:9][C:8]3[C:7](=[CH:10][CH:1]=[CH:2][CH:3]=3)[CH:6]=4)[C:11](=[O:12])[C:20]=2[CH:19]=[CH:18][CH:17]=1

Komponenten

3

Edukt 2

HCID 113051,4-NaphthalenediolHCID 964002,3-Naphthalenedicarboxaldehyde

Produkt 1

HCID 106862375,14-Pentacenedione

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a flame-dried flask was added 2,3-naphthalenedicarboxaldehyde (1 molar equivalent (0.29 g, 1.57 mmol)) and 1,4-dihydroxynaphthalene (1 molar equivalent (0.25 g, 1.57 mmol)) these reagents were flushed with nitrogen for 15 minutes before anhydrous pyridine (5 ml) was added. The resulting solution was stirred at 120° C. with stirring for 24 hours. On cooling, the solid product was filtered off and washed successively with methanol (10 ml), 10% copper sulphate solution (10 ml), water (10 ml) and acetone (10 ml) and dried in vacuum oven. The product was an orange/brown solid (0.14 g, 29%) and was greater than 90% pure by HPLC. 1H NMR (D8-THF) δ 9.09 (2H, s, H—Ar), 8.87 (2H, s, H—Ar), 8.38 (2H, m, H—Ar), 8.15 (2H, m, H—Ar), 7.87 (2H, m, H—Ar) and 7.61 ppm (2H, m, H—Ar).

Aufarbeitung

  1. customwere flushed with nitrogen for 15 minutes before anhydrous pyridine (5 ml)
  2. additionwas added
  3. stirringwith stirring for 24 hours
  4. temperatureOn cooling
  5. filtrationthe solid product was filtered off
  6. washwashed successively with methanol (10 ml), 10% copper sulphate solution (10 ml), water (10 ml) and acetone (10 ml)
  7. customdried in vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-2f83e319d7f2484196094a79e4c9ba4b
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119804B2

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