Acetic Acid → HCID 178511211, compound

Participants

Reaction Conditions

Reaction Steps

At room temperature, 5.61 g (0.10 mol) of freshly distilled acrolein are added to 10.21 g (0.10 mol) of acetic anhydride. At 25-30° C., 13.61 g (0.10 mol) of diethyl methanephosphonate are subsequently added dropwise. The mixture is stirred at 30° C. for 2 hours and then, at 25-28° C., added dropwise to a solution of 4.9 g (0.10 mol) of sodium cyanide and 10.7 g (0.20 mol) of ammonium chloride in 50 ml of ammonia (25% strength). After 2 hours at 30° C., the crude aminonitrile is added dropwise to 200 ml of hydrochloric acid (37% strength). The mixture is subsequently heated under reflux for 2 hours, while ethanol and acetic acid are distilled off. The mixture is concentrated using a rotary evaporator, a pH of approximately 9 is set using ammonia solution and the product is purified by crystallization from methanol. This gives 19.4 g (98% of theory) of 2-amino-4-(hydroxymethylphosphinyl)butyric acid, ammonium salt.

Provenance & Evidence