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

Participants

Reaction Conditions

Reaction Steps

To a solution of 9-amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthracene (50 mg) in conc. hydrochloric acid (2 ml) and water (2 ml) was added a solution of sodium nitrite (112 mg) in water (1.0 ml) at 0° C. The resulting mixture was stirred at 0° C. for 1 hour and at room temperature 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 (35 mg).

Provenance & Evidence