9-Amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthracene → 9,10-Dihydro-9,10-methanoanthracene-9-carboxaldehyde

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Reaction Steps

To a solution of 9-amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthracene (3.0 g) in acetic acid (240 ml) was added a solution of sodium nitrite (6.7 g) in water (120 ml) at 2° - 5° C., and the resulting mixture was stirred at the same temperature for 1 hour and at 95° - 105° C. for 5 hours. The reaction mixture was diluted with water and extracted with benzene. The benzene layer was washed with water, dried over sodium sulfate and evaporated to dryness to give crude crystals of 9-formyl-9,10-dihydro-9,10-methanoanthracene (2.8 g), which were recrystallized to give colorless crystals (2.45 g), M.P. 99° - 100° C. Further, purification by recrystallization gave analytically pure 9-formyl-9,10-dihydro-9,10-methanoanthracene, M.P. 102.5° C.

Provenance & Evidence