Synthesis, purification, and characterization of ethylene glycol ether aldehydes

ORGN 89

Aaron D. Gross, graa0301@stcloudstate.edu, Lakshmaiah Sreerama, lsreerama@stcloudstate.edu, and Daniel Gregory, dgregory@stcloudstate.edu. Department of Chemistry, St. Cloud State University, Robert H Wick Science Building, 720 Fourth Avenue South, St. Cloud, MN 56301
Ethylene glycol ethers (EGE) are a group of solvents that are widely used in aerosols and cleaning material for both industry and commercial use, which leads to high exposure to humans. A hypothesized route of metabolism of EGE's is oxidation to the corresponding aldehyde via alcohol dehydrogenases followed by oxidation to its corresponding carboxylic acid via aldehyde dehydrogenases. This work is part of a collaborative project aimed at elucidating the role of aldehydes dehydrogenases. The synthesis, purification, and characterization for several alkoxyethanals will be presented. Briefly the aldehydes were produced via a swern oxidation of the corresponding alcohol. The purification of the aldehydes was accomplished by vacuum distillations or column chromatography. Characterization and purity of the resulting aldehyde was achieved using 300 MHz H1NMR and gas chromatography.