1,4-Naphthalenediol → 5,14-Pentacenedione

HRID 2104934

반응식

HRID 2104934 반응식
[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

참가 물질

3

반응물 2

HCID 113051,4-NaphthalenediolHCID 964002,3-Naphthalenedicarboxaldehyde

생성물 1

HCID 106862375,14-Pentacenedione

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ad20a59def71418baf22f34e7e9161e0
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576208B2

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