2-Chloroanthraquinone → 2-Methoxyanthraquinone

HRID 931873

反応式

HRID 931873 の反応式
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[CH3:18][O-:19].[Na+]>CN(C)C=O.CO>[CH3:18][O:19][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1

参加物

5

反応物 2

HCID 85532-ChloroanthraquinoneHCID 10942334Sodium Methoxide

生成物 1

HCID 186462-Methoxyanthraquinone

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

First, the intermediate 2-methoxy-9,10-anthraquinone was prepared. A solution of 2-chloro-9,10-anthraquinone (10.08 g, 42 mmol) in 100 mL of N,N-dimethylformamide was treated with 25 mL of 25% sodium methoxide in methanol. The stirred reaction mixture was heated in a 120° C. oil bath for 6 h under nitrogen, then cooled to ambient. The product was precipitated into aqueous HCl (0.5 M, 250 mL), collected, washed with water and dried. The product was purified by recrystallization from a mixture of toluene and heptane to provide 1.6 g (16%) of a light yellow solid. This intermediate was characterized by 1H NMR: (300 MHz, CDCl3) δ 4.00 (s, 3H), 7.28 (d, 1H), 7.29 (d, 1H), 7.70 (m, 2H), 8.26 (s, 1H), 8.30 (m, 2H).

後処理

  1. customThe stirred reaction mixture
  2. temperaturecooled
  3. customThe product was precipitated into aqueous HCl (0.5 M, 250 mL)
  4. customcollected
  5. washwashed with water
  6. customdried
  7. customThe product was purified by recrystallization from a mixture of toluene and heptane

出典と根拠

ORDレコード
ord-601ab51f2a804464a2c4b8ecaac37685
出典データセット
uspto-grants-2016_03
特許番号
US09298088B2

関連ノート

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