SnCl2 reduction of phenyl-2-nitropropenes to Phenyl-2-Propanones

18,1g (100mmol) 1-(2-fluorophenyl)-2-nitropropene was added dry in portions to 49,5g (220mmol) SnCl2 x 2 H2O suspended in 75ml EtOAc while the reaction temperature was kept between 20-40°C by a cold water bath. When all nitropropene was added and the color had changed to white (5 min) the EtOAc solution was transferred to a rb flask containing 250ml water and 50 ml hydrochloric acid. The EtOAc was removed by distillation under diminished pressure and the aqueous suspension of oxime and tin salts was allowed to stir at 80°C for 1 hour. The water phase was now steam distilled to remove the ketone. When no more oily drops came over the distillate was extracted with DCM. The DCM extracts was dried over MgSO4 and the DCM removed by distillation leaving a quite pure ketone as a colorless oil with with a nice aromatic smell.

Yield: 13,5g (89%) 1-(2-fluorophenyl)-2-propanone, Purity 98% (HPLC), bp 47°C/0.05mmHg