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

HRID 83107

반응식

HRID 83107 반응식
[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

참가 물질

5

반응물 2

HCID 359PhloroglucinolHCID 71043-Hydroxy-2-naphthoic acid

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 24813Phosphorus oxychloride용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-98e6d9d9540844bd8f0349e988c593d1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846749B2

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