Dimethylformamide → 9-ethyl-9H-carbazole-3,6-dicarbaldehyde

Participants

Reaction Steps

Dimethylformamide (DMF) (271 ml, 3.5 mol, from Aldrich Chemicals, Milwaukee, Wis.) was added to a 1-liter, 3-neck round bottom flask equipped with a mechanical stirrer, a thermometer, and a dropping funnel. The flask and its content were cooled on a salt/ice bath. When the temperature of the solution inside the flask reached 0° C., phosphorus oxychloride (POCl3, 326 ml, 3.5 mol, from Aldrich Chemicals, Milwaukee, Wis.) was added slowly using a dropping funnel. During the addition of POCl3, the temperature inside the flask was kept at or below 5° C. After completing the addition of POCl3, the reaction mixture was allowed to warm to room temperature. 9-Ethylcarbazole (97 g, 0.5 mole, from Aldrich chemicals, Milwaukee, Wis.) was added and the flask was kept at 90° C. for 24 hours using a heating mantle. Then, the reaction mixture was cooled to room temperature. The cooled reaction mixture was added slowly to a 4.5 liter beaker containing a solution of 820 g sodium acetate dissolved in 2 liters of water. The beaker was stirred and cooled on an ice bath for 3 hours. The brownish solid obtained was filtered and washed repeatedly with water and, subsequently, with a small amount of ethanol (50 ml). The resulting product, 9-ethyl-3,6-carbazoledicarbaldehyde, was recrystallized once from a mixture of tetrahydrofuran and isopropanol and dried under vacuum in an oven heated at 50° C. for 6 hours. The yield was 65 g (52%).

Provenance & Evidence