1,4-Naphthalenediol → 5,14-Pentacenedione

HRID 1177832

Reaction equation

HRID 1177832 reaction equation
[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

Participants

3

Reactant 2

HCID 113051,4-NaphthalenediolHCID 964002,3-Naphthalenedicarboxaldehyde

Product 1

HCID 106862375,14-Pentacenedione

Conditions

Temperature
120 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-cf932bf2ed02442ea5534c1203e46d05
Source dataset
uspto-grants-2010_11
Patent number
US07842942B2

Linked notes

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