A two-step synthesis of deuterium labeled 8, 8, 9, 9-d4-hexadecane from nonanoic acid

Labeled compounds are essential in elucidating metabolic mechanisms and reaction pathways. A two-step synthesis of deuterium-labeled 8, 8, 9, 9-d4-hexadecane from nonanoic acid is described here. The synthesis procedures involved hydrogendeuterium exchange of nonanoic acid with 3.00?m DCl-D2O and then Kolbe electrolysis of the deuterated nonanoic acid to achieve the desired n-alkane that was confirmed by gas chromatography-mass spectrometry and 1H nuclear magnetic resonance. This method might provide an alternative route for the preparation of specifically deuterated alkanes of different chain lengths (C?>?4) in which deuterium atoms are located at two adjacent carbons of the alkane's carbon chain. Copyright (c) 2012 John Wiley & Sons, Ltd.