Synthesis of four n-alkanes with terminal dipolar substituents

12-Nitrododecanol, 1,12-dinitrododecane, 1,24-dinitrotetracontane and 2,15-diaminohexadecan-1,16-dioioc acid were prepared from the common intermediate 12-bromododecanol. This bromoalcohol, being prepared from cyclododecanone, is free of homologous bifunctional impurities. The functionalised 24 carbon chain was prepared by a Wittig reaction of 12-bromododecanal with the triphenylphosphonium salt of 12-bromododecanal ethylene acetal using ‘naked’ carbonate anion to provide the base. The resulting bromoacetal was converted to 24-bromotetracont-12-enol, both this and the 12-bromododecanol were converted to the corresponding α,ω-di-iodides and then to the desired α,ω-dinitro compounds. The α-amino acid functionality can be introduced on an α,ω-dihalide with the anion of either diethyl 2-acetylaminopropan-1,3-dioate or benzylidene glycine ethyl ester. Also detailed is the previously unreported reduction of a carboxylic acid to an alcohol by borane-dimethyl sulphide in dichloromethane.