Hydrochloric Acid → 1-Propene-1,1,3-tricarbonitrile, 2-phenyl-

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Reaction Steps

A mixture of 250 grams (1722 mmol, 1 eq) of benzoylacetonitrile, 284 grams (270 mL, 4306 mmol, 2.5 eq) of malononitrile and 138 grams (1784 mmol, 1.04 eq) of ammonium acetate in 2500 mL of ethanol was heated to reflux for 1.5 hours and then cooled to room temperature. To this mixture was added 190 mL of 12M hydrochloric acid dropwise with cooling (ice/water bath). The mixture was placed in a separate flask and a solid formed and filled the flask. To this mixture was added 3300 mL of water with stirring. The solid was collected and washed with 2 liters of water and triturated with 1200 mL of ethanol to give 203.3 grams (61% yield) of pure 2-phenyl-1,1,3-tricyanopropylene, mp 105°-107° C.

Provenance & Evidence