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

HRID 2413639Notes

Reaction equation

HRID 2413639 reaction equation
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

Participants

4

Reactant 1

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

Product 1

HCID 1507891-Anthracenecarboxylic AcidYield 82%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 14923Ammonium HydroxideSolvent

Procedure

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 (15A, 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. 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, cooled and the excess Zn removed by filtration. The filter cake was washed with more NH4OH solution (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 1× from methoxyethanol/H2O (containing 1% conc. HCl), filtered and dried at 75°, to give 65 g (82%) 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.).

Workup

  1. customTo a 5 L 3-neck flask fitted with condenser
  2. temperatureThe mixture was heated slowly
  3. customreached 85°
  4. temperatureThe reaction was heated an additional 1 h
  5. temperaturecooled
  6. customthe excess Zn removed by filtration
  7. washThe filter cake was washed with more NH4OH solution (100 mL)
  8. customwas carefully acidified to pH 1 with conc. HCl (added 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 1× from methoxyethanol/H2O (containing 1% conc. HCl)
  13. filtrationfiltered
  14. customdried at 75°

Sources & evidence

ORD record
ord-4f539a978275425c9debf0185782fd75
Source dataset
uspto-grants-1988_01
Patent number
US04719049

Reaction notes

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