Convenient syntheses of bifunctional C12-acyclic compounds from cyclododecanone

Abstract

The conversion of cyclododecanone by convenient, non-hazardous, and high-yielding reactions into a set of useful C₁₂-bifunctional intermediates is described. Baeyer–Villiger oxidation and hydrolysis give a hydroxy acid, successively converted into the bromo acid, bromo alcohol, crude bromo aldehyde, pure bromo aldehyde ethylene acetal, and pure bromo aldehyde. Preferred reagents for the transformation CO₂H → CHO are borane–dimethyl sulphide followed by dimethyl sulphoxide–oxalyl dichloride–triethylamine.