2-Nitro-1-phenylpropene [705-60-2-A] C9H9NO2
About the reaction: Nitroethane, as a CH-acidic compound, adds to the carbonyl carbon of benzaldehyde, with water being eliminated and a double bond being formed. The water formed is removed from the reaction mixture using a water separator. The product (a styrene) can be reduced to amphetamine.
Procedure: In a 1500-ml round-bottom flask, first place 300 ml of xylene (isomer mixture), 202.9 ml (2.82 mol) of nitroethane, 284.3 ml (2.89 mol) of freshly distilled benzaldehyde, and 15 ml of n-butylamine. Equip the flask with a water separator on which a reflux condenser is mounted. Heat the mixture to boiling for 50 hours in an oil bath, during which about 50 ml of water collects in the water separator. After 50 hours (* see note), allow to cool, filter off the precipitated crystals, wash with xylene, and dry in the air. In this way, 170 g of 2-nitro-1-phenylpropene is obtained. The filtrate is then concentrated, and the oily residue is recrystallized from methanol. This yields another 220 g of 2-nitro-1-phenylpropene. The total yield is 390 g (83% of the theoretical yield) of a product melting at 65 °C.
Note: Nitroalkenes are sensitive and tend to polymerize. There are valid doubts about the long reaction time of 50 hours. Shorter refluxing and reaction control by thin-layer chromatography are recommended.
Source: Boberg, F.; Schultze, G. R. Chem. Ber. 1957, 90, 1221
Alternative Syntheses: Rhodium/Phenyl-2-nitropropene
Delivered by: Mephisto
Created: 01/05/2006
Last updated: 31/05/2013
Other names: (2-Nitro-1-propenyl)benzene; (2-Nitropropenyl)benzene; β-Methyl-β-nitrostyrene; 1-(2-Nitropropenyl)benzene; 1-Phenyl-2-nitro-1-propene; 1-Phenyl-2-nitro-2-methylethene; 1-Phenyl-2-nitropropene; 2-Nitro-1-phenyl-1-propene; 2-Nitro-1-phenylpropene; 2-Nitro-3-phenyl-2-propene; NSC 2014; P2NP