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

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Reaction Steps

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.).

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