Hydrochloric Acid → (2Z)-4-(Dodecylamino)-4-oxo-2-butenoic acid

Participants

Reaction Conditions

Reaction Steps

30 g of pyridine are added to a solution of 83 g of maleic anhydride in 700 ml of dichloromethane at room temperature. A solution of 122 g of n-dodecyl-amine and 70 g of pyridine in 800 ml of dichloro-methane is then added dropwise in 15 min, during which the temperature rises to 39° C. The mixture is then refluxed for 30 min, cooled to 25° C. and 210 ml of 32% by weight aqueous hydrochloric acid are cautiously added. The aqueous phase is separated off at 35° C., and the organic phase is washed three times with 200 ml of water each time at 35° C., dried over sodium sulfate and crystallized at 10° C. 180 g (96%) of N-dodecylmaleamic acid are obtained in the form of colorless waxy crystals. The product is pure by NMR and gives a clear solution in dilute sodium hydroxide solution.

Provenance & Evidence