9,10-Dioxo-9,10-dihydroanthracene-1-carboxylic acid → 1-Anthracenecarboxylic Acid

HRID 2413606노트

반응식

HRID 2413606 반응식
O=[C:2]1[C:15]2[C:14]([C:16]([OH:18])=[O:17])=[CH:13][CH:12]=[CH:11][C:10]=2[C:9](=O)[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2>[Zn].[NH4+].[OH-]>[C:14]1([C:16]([OH:18])=[O:17])[C:15]2[C:10](=[CH:9][C:8]3[C:3]([CH:2]=2)=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:11]=[CH:12][CH:13]=1

참가 물질

4

반응물 1

HCID 2201079,10-Dioxo-9,10-dihydroanthracene-1-carboxylic acid

생성물 1

HCID 1507891-Anthracenecarboxylic Acid

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 14923Ammonium Hydroxide용매

실험 절차

To a 5 L 3-neck flask fitted with condenser, thermometer, and overhead stirrer was added 9,10-dihydro-9,10-dioxo-1-anthracenecarboxylic acid (90 g, 0.357 mol), Zn dust (Mallinckrodt, 250 g, 3.82 mol), CuSO4.5H2O (Mallinckrodt, 5 g), and 28% NH4OH (Mallinckrodt, 2500 mL). The mixture was heated slowly until a dark-red solution occurred as the temperature reached 85°. After 3.5 h the color of the solution faded to yellow. The reaction was heated an additional 1 h, and then cooled and the excess Zn filtered. The filter cake was washed with more NH4OH (100 mL) and then discarded. The filtrate was carefully acidified to pH 1 with conc. HCl added in portions over 1 h affording a light-green precipitate which was separated by filtration. The solid was washed with H2O (200 mL) and then recrystallized once from methoxyethanol/H2O (with a small amount of HCl) to give 65 g (82%) filtered, and dried at 75° of 1-anthracenecarboxylic acid mp 249°-250°, (C,H), (lit. mp 245°, Chemistry of Carbon Compounds IIIb, edited by E. H. Rodd, 1373 (1956), Elsevier, N.Y.).

후처리

  1. customTo a 5 L 3-neck flask fitted with condenser
  2. temperatureThe mixture was heated slowly until a dark-red solution
  3. customreached 85°
  4. temperatureThe reaction was heated an additional 1 h
  5. temperaturecooled
  6. filtrationthe excess Zn filtered
  7. washThe filter cake was washed with more NH4OH (100 mL)
  8. additionadded in portions over 1 h
  9. customaffording a light-green precipitate which
  10. customwas separated by filtration
  11. washThe solid was washed with H2O (200 mL)
  12. customrecrystallized once from methoxyethanol/H2O (with a small amount of HCl)
  13. customto give 65 g (82%)
  14. filtrationfiltered
  15. dry with materialdried at 75° of 1-anthracenecarboxylic acid mp 249°-250°, (C,H), (lit. mp 245°, Chemistry of Carbon Compounds IIIb

출처 및 근거

ORD 기록
ord-395079d70d514aff9c07f484beaead9e
출처 데이터셋
uspto-grants-1988_01
특허 번호
US04719047

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