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

HRID 1381727Notes

Reaction equation

HRID 1381727 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 1500 mL of glacial HOAc at 90° and stirred with a mechanical stirrer. After cooling to 80° solid CrO3 (Mallinckrodt, Co., 2nd and Mallinckrodt St., St. Louis, MO, 63147, 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 2 L of hot methoxyethanol and filtered through Celite (Trade Mark of Johns-Manville Co., Denver, CO, 80110) to remove a black solid residue. The volume of the solution was reduced to ~75 mL (some solid formed) and diluted with 100 mL CH3OH to give the product. This material was filtered 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, N.Y.).

Workup

  1. additionwas added in ~5 g portions over about 4 h
  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 2 L of hot methoxyethanol
  9. filtrationfiltered through Celite (Trade Mark of Johns-Manville Co., Denver, CO, 80110)
  10. customto remove a black solid residue
  11. customformed) and
  12. customto give the product
  13. filtrationThis material was filtered

Sources & evidence

ORD record
ord-86da559915b443e6adfcf385eb0cf45b
Source dataset
uspto-grants-1989_02
Patent number
US04803226

Reaction notes

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