A simple synthesis for 2-acetonylcyclododecanone

A simple method is proposed for the alkylation of cyclododecanone by propargyl halides under phase transfer catalysis conditions with the formation of 2-propargylcyclododecanone. The hydration of 2-propargylcyclododecanone upon catalysis by mercury compounds leads to either 14-methyl-13-oxabicyclo[10.3.0]-pentadeca-1(12),14-diene or 2-acetonylcyclododecanone depending on the reaction conditions. Both these compounds are also readily obtained from 2-(2-chloropropen-2-yl)cyclododecanone which readily forms upon the alkylation of cyclododecanone by 1,2-dichloropropene under phase transfer catalysis conditions.Translated from Izvestiya Akademil Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 963–965, April, 1991.