Question

How will you obtain benzene from benzaldehyde

Answer 1

To a suspension of 1.58 g (10 mmol) of Bis(diformylamino)methane in 20 ml of benzene, 5.35 g (40 mmol) of aluminum chloride was added at 20°C. The mixture was stirred for 66 h at the same temperature. The mixture is poured slowly under stirring in 500 ml of water. After stirring for one hour, a steam distillation is carried out. The resulting distillate is extracted twice with 50 ml of chloroform. The combined organic phases are dried with sodium sulfate. After filtering off the drying agent, the organic solvents were removed in vacuo and the residue was fractionally distilled. Yield: 1.5 g (71%) of colorless liquid. Bp. 180°C; nD20 = 1.5440.

Answer 2

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To a suspension of 1.58 g (10 mmol) of Bis(diformylamino)methane in 20 ml of benzene, 5.35 g (40 mmol) of aluminum chloride was added at 20°C. The mixture was stirred for 66 h at the same temperature. The mixture is poured slowly under stirring in 500 ml of water. After stirring for one hour, a steam distillation is carried out. The resulting distillate is extracted twice with 50 ml of chloroform. The combined organic phases are dried with sodium sulfate. After filtering off the drying agent, the organic solvents were removed in vacuo and the residue was fractionally distilled. Yield: 1.5 g (71%) of colorless liquid. Bp. 180°C; nD20 = 1.5440.