5g (19,8mmol) 1-(2,4,5-trimethoxyphenyl)-2-nitropropene
12,3g (55mmol) tin(II)chloride dihydrate
15ml conc. hydrochloric acid
20ml toluene
15ml water
100ml EtOAc
Tin(II)chloride was dissolved in 15ml water and 15ml conc hydrochloric acid and the resulting solution was added to a 200ml rb flask containing 20ml toluene and 5g substrate. The mixture was heated to 80 deg C on a water bath with good stirring for 1,5 hours. During this time the color changed from a deep yellow to dark orange and then to light yellow.
After 1,5 hours 200ml water was added and the toluene was removed by steam distillation. The now bright yellow aqueous phase containing dark yellow oily droplets was saturated with NaCl and extracted with 2x50ml EtOAc which removed all color. The ethyl acetate was washed once with 50ml saturated NaHCO3 solution, once with 50ml water, once with brine and then dried with MgSO4. The solvent was removed in a rotovap leaving 3,7g of a yellow oil which slowly partially solidified to something reminding of honey.
Yield; 3,7g (83,8%) 1-(2,4,5-trimethoxyphenyl)-2-propanone