N-ethyl carbazole → Octanal

Participants

Reaction Steps

To 7.83 g (40.1 mmol) of N-ethylcarbazole in 40 mL of CH2Cl2 are added 5.91 g (42.0 mmol) of benzoyl chloride and 5.88 g (44.1 mmol) of AlCl3. After stirring for 4 h at room temperature, 6.89 g (42.3 mmol) of octanoyl chloride and 5.92 g (44.4 mmol) of AlCl3 are added. This reaction mixture is stirred at room temperature for 4.5 h. Then, the reaction mixture is poured into ice-water. The products are extracted with CH2Cl2. The CH2Cl2 layer is washed with water, saturated NaHCO3 aq. solution and with brine, followed by drying over anhydrous MgSO4. Purification by column chromatography on silica gel with CH2Cl2-hexane(1:1) as eluent affords 12.7 g of a white solid (74.2%).

Provenance & Evidence