Phloroglucinol → 1,3-dihydroxy-12H-benzo(b)xanthen-12-one

HRID 83107

反応式

HRID 83107 の反応式
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:15]1([CH:23]=[C:21](O)[CH:20]=[C:18]([OH:19])[CH:17]=1)[OH:16]>[Cl-].[Cl-].[Zn+2].O=P(Cl)(Cl)Cl>[OH:16][C:15]1[C:23]2[C:12](=[O:14])[C:3]3[CH:4]=[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:10]4=[CH:11][C:2]=3[O:1][C:21]=2[CH:20]=[C:18]([OH:19])[CH:17]=1

参加物

5

反応物 2

HCID 359PhloroglucinolHCID 71043-Hydroxy-2-naphthoic acid

生成物 1

HCID 107077051,3-dihydroxy-12H-benzo(b)xanthen-12-one収率 9.8%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 24813Phosphorus oxychloride溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3-hydroxy-2-naphthoic acid (2.0 g, 10.63 mmol), phloroglucinol (1.34 g, 10.63 mmol), ZnCl2 (3.30 g, 24.24 mmol) and POCl3 (40 mL) was stirred under reflux at 80° C. for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and was very slowly added to 1 L of ice water. The resulting solid was allowed to stand (1 d), filtered, washed with water, and then dried under reduced pressure to obtain an ocherous compound. This compound was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v)) to give the title compound (289 mg, 9.8%) as a yellow solid.

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. custom(1 d)
  3. filtrationfiltered
  4. washwashed with water
  5. customdried under reduced pressure
  6. customto obtain an ocherous compound
  7. customThis compound was separated
  8. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v))

出典と根拠

ORDレコード
ord-98e6d9d9540844bd8f0349e988c593d1
出典データセット
uspto-grants-2014_09
特許番号
US08846749B2

関連ノート

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