Acetic Acid → p-Chloro-beta-nitrostyrene

Participants

Reaction Conditions

Reaction Steps

To a solution of 57 g (98%, 0.397 mol) of 4-chlorobenzaldehyde and 24.8 g (0.398 mol) of nitromethane in 461 ml of toluene cooled to 5° C. were added 107.2 g of a solution of sodium methylate in methanol (30%; 0.596 mol) during 45 min. The mixture was subsequently stirred at 0 to 5° C. for 2 h. The suspension was cooled to 0° C. and then 40.0 g (0.666 mol) of anhydrous acetic acid were added, this causing the temperature to rise to 7° C. The mixture was diluted with 290 ml of toluene and methanol was removed by distillation at 100 mbar. 205 g (99%, 1.988 mol) of acetic anhydride were added, the mixture was heated to 50° C. and stirred for 15 h at this temperature. For workup, the mixture was poured onto 725 g of ice water, the phases were separated and the organic phase was extracted with alkaline water (pH 8.5). After concentration at 10 mbar, 74.8 g of the title compound in form of a yellow solid were obtained.

Provenance & Evidence