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Reber, Keith P. ; Sivey, John D. ; Vollmuth, Matthew ; Gujarati, Priyansh D. ( , Journal of Labelled Compounds and Radiopharmaceuticals)
Parabens are antimicrobial additives found in a wide array of consumer products. However, the halogenated compounds formed from parabens during wastewater disinfection are a potential environmental concern. In order to identify these transformation products and investigate their mechanism of formation, a synthetic route to ethyl parabens labeled with the stable isotope carbon‐13 at specific positions within the benzene ring was developed. This efficient two‐step procedure starts from commercially available13C‐labeled phenols and involves (1) initial acylation of the phenol via a Houben–Hoesch reaction with trichloroacetonitrile followed by (2) a modified haloform reaction of the resulting trichloromethyl ketone to afford the corresponding13C‐labeled ethyl parabens in 65%–80% overall yield. The scope of the modified haloform reaction was also investigated, allowing for the synthesis of other parabens derived from primary or secondary alcohols, including13C‐ and deuterium‐labeled esters. In addition, 4‐hydroxybenzoic acid can be formed directly from the common trichloromethyl ketone intermediate upon treatment with lithium hydroxide. This protocol complements existing methods for preparing13C‐labeled paraben derivatives and offers the specific advantages of exhibiting complete regioselectivity in the Houben–Hoesch reaction (to form the
para ‐disubstituted product) and avoiding the need for protecting groups in the modified haloform reaction that forms the paraben esters.