1,4-Naphthalenediol → 5,14-Pentacenedione

HRID 2104934

反応式

HRID 2104934 の反応式
[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

参加物

3

反応物 2

HCID 113051,4-NaphthalenediolHCID 964002,3-Naphthalenedicarboxaldehyde

生成物 1

HCID 106862375,14-Pentacenedione

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ad20a59def71418baf22f34e7e9161e0
出典データセット
uspto-grants-2009_08
特許番号
US07576208B2

関連ノート

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