Carbon Dioxide → 9,10-Dioxo-9,10-dihydroanthracene-1-carboxylic acid

HRID 1381774Notes

Reaction equation

HRID 1381774 reaction equation
C1[C:17]2=[C:18]3[C:8]([C:9]([C:11]4[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=4)=[O:10])=[CH:7][CH:6]=[CH:5][C:4]3=CC=1.[C:19](=[O:21])=[O:20].[OH2:22]>CC(O)=O.CO>[O:10]=[C:9]1[C:8]2[C:7]([C:19]([OH:21])=[O:20])=[CH:6][CH:5]=[CH:4][C:18]=2[C:17](=[O:22])[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

6

Reactant 3

HCID 280Carbon Dioxide2×HCID 962WaterHCID 6697Benzanthrone

Product 1

HCID 2201079,10-Dioxo-9,10-dihydroanthracene-1-carboxylic acidYield 46%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The purified benzanthrone (63.7 g, 0.277 mol) was dissolved in glacial HOAc (1.5 L) (heated to 90°) and stirred with a mechanical stirrer. After cooling to 80°, solid CrO3 (Mallinckrodt, 200 g, 2 mol) was added in 5 g portions over about 4 h. The exothermic reaction maintained the mixture at 80° during this time and CO2 was evolved. After CO2 evolution ceased and the reaction temperature fell, the heating mantle was reapplied and the reaction stirred at 75° for an additional 6 h. The reaction was cooled to RT and stirred overnight. H2O (1.5 L) was then added to the dark-green solution. The reaction was then filtered to give a deep brown solid which was washed with CH3OH (200 mL) until the washings were colorless. The resulting solid was dissolved in hot 2-methoxyethanol (2 L) and filtered through Celite® to remove a black solid residue. The volume of the solution was reduced to 75 mL (some solid formed) and diluted with CH3OH (100 mL to give the product. This material was removed by filtration to give 32.0 g (46%) of golden brown 9,10-dihydro-9,10-dioxo-1-anthracenecarboxylic acid mp 287°-289°, (C, H), (lit. mp 293°-294°, Chemistry of Carbon Compounds IIIb, edited by E. H. Rodd, 1419 (1956), Elsevier, New York).

Workup

  1. temperatureAfter cooling to 80°
  2. customThe exothermic reaction
  3. stirringthe reaction stirred at 75° for an additional 6 h
  4. stirringstirred overnight
  5. filtrationThe reaction was then filtered
  6. customto give a deep brown solid which
  7. washwas washed with CH3OH (200 mL) until the washings
  8. dissolutionThe resulting solid was dissolved in hot 2-methoxyethanol (2 L)
  9. filtrationfiltered through Celite®
  10. customto remove a black solid residue
  11. customformed) and
  12. customto give the product
  13. customThis material was removed by filtration

Sources & evidence

ORD record
ord-2b3f713ccb8b45b985058b20313d492c
Source dataset
uspto-grants-1989_02
Patent number
US04803221

Reaction notes

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