Collect. Czech. Chem. Commun. 1981, 46, 1262-1271

Synthesis of 2-allyl-2-ethylsuccinic anhydride

Josef Hájíček and Jan Trojánek

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


The paper describes a synthesis of 2-allyl-2-ethylsuccinic anhydride (I), starting from ethyl cyanoacetate, with the Wolff rearrangement of diazo ketone XVI as the key step. The unsuccessful attempts at the synthesis are also described. The mechanism leading to an anomalous product of the reaction between cyanohydrine VI and sodium ethylcyanoacetate, viz. ethyl 2-cyano-3-methyl-5-oxoheptanoate (VIII), is also discussed.