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One-Pot Oxidative Cleavage of Olefins to Synthesize Carboxylic Acids by a Telescoped Ozonolysis-Oxidation Process

Brian M. Cochran*

*Synthetic Technologies, Process Development, Amgen, Inc., One Amgen Center Drive, Thousand Oaks, CA 91320, USA, Email: cochranbamgen.com

B. M. Cochran, Synlett, 2016, 27, 245-248.

DOI: 10.1055/s-0035-1560659 (free Supporting Information)


Abstract

A mild one-pot ozonolysis-oxidation process enables the synthesis of carboxylic acids from alkenes. Conducting the ozonolysis in an aqueous organic solvent eliminates secondary ozonide formation and the intermediates generated are readily converted into a carboxylic acid by adding sodium chlorite. The desired acids are isolated in high purity and high yield by simple extraction after a reductive quench.

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Key Words

ozonolysis, carboxylic acids, green chemistry, alkenes, oxidation, ozone, sodium chlorite


ID: J60-Y2016