Phthalaldehyde → 6,13-Pentacenequinone

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of 62.7 grams (0.559 mmoles, 1.0 equivalents) of cyclohexan-1,4-dione and 150 grams of o-phthalaldehyde (1.12 mmoles, 2.0 equivalents) in 2000 mL of ethanol was heat to 28° C. To this solution was added 220 mL of a 1M aqueous solution of sodium hydroxide. The reaction temperature increased to 47° C. during the addition. The mixture was then heated at 40° C. for 4 hours. The mixture was cooled and a yellow solid precipitate was collected. The solid was stirred in 2000 mL of N,N-dimethylformamide and heated to 50° C. for 2 hours. The mixture was cooled to room temperature (i.e., 20° C. to 25° C.) and the yellow solid was collected and washed with N,N-dimethylformamide, then with acetone and dried to give 108.3 grams (62 mole percent yield) of a bright yellow solid.

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