The main goal of this research project was to prepare a series of fatty acid dimethyl acetals, CH3(CH2)n CH(OMe)2, n = 14, 16, 17. The compounds were needed for peak verification in methylated lipid extracts of Mississippi River biota previously analyzed by GC-MS. The mass spectra of dimethyl acetals are dominated by the dimethoxymethyl cation +CH(OMe)2, m/z = 75, and the M+ peaks are not present. Thus, authentic samples of the acetals were needed to validate tentative assignments made to unknown peaks in the lipid analyses. The corresponding fatty acid methyl esters were reduced using diisobutylaluminum hydride to form fatty aldehydes, which were then methylated with boron trifuloride/methanol in an attempt to produce the fatty acid dimethyl acetals in a single pot.

Synthesis of fatty acid dimethyl acetals from fatty acid methyl esters by reduction with DIBAL and methylation with BF<sub>3</sub>

243rd National Meeting (2012)

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Synthesis of fatty acid dimethyl acetals from fatty acid methyl esters by reduction with DIBAL and methylation with BF3

Synthesis of fatty acid dimethyl acetals from fatty acid methyl esters by reduction with DIBAL and methylation with BF₃