Synthesis of the α,α′‐dehydrodimer of methyl octanoate and the β,β′‐dehydrodimer of methyl nonanoate and their mass and NMR‐spectra

Abstract

AbstractDimethyl 7,8‐tetradecanedicarboxylate and 7,8‐di(methoxycarbonylmethyl)‐tetradecane have been synthesized. 2‐Bromooctanoic acid ester was coupled to ethyl cyanoacetate and the reaction product converted with hexyl iodide. Saponification, decarboxylation with copper and acid hydrolysis yielded the octanoic acid dehydrodimer. 7,8‐Di(hydroxymethyl)tetradecane was converted with tosyl chloride and the product treated with KCN to give a dicyanide.The purity of the compounds was checked with GLC. Their mass spectra showed different characteristic fragmentation patterns. In the NMR spectra δ‐shift values were different.