Continuous Flow Oxidation of Alcohols and Aldehydes Utilizing Bleach and Catalytic Tetrabutylammonium Bromide
Name
Leduc Jamison OPRD 2012.pdf
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438.18 KB
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Author(s)
Leduc, Andrew B.
Jamison, Timothy F.
Date Issued
June 2011
Journal
Organic Process Research & Development
Publisher
American Chemical Society (ACS)
Citation
Leduc, Andrew B., and Timothy F. Jamison. “Continuous Flow Oxidation of Alcohols and Aldehydes Utilizing Bleach and Catalytic Tetrabutylammonium Bromide.” Organic Process Research & Development 16.5 (2012): 1082–1089.
Version
Author's final manuscript
Abstract
We report a method for the oxidation of a range of alcohols and aldehydes utilizing a simple flow system of alcohols in EtOAc with a stream of 12.5% NaOCl and catalytic Bu[subscript 4]NBr. Secondary alcohols are oxidized to ketones, aldehydes are oxidized directly to methyl esters in the presence of methanol, and benzylic alcohols are oxidized to either benzaldehydes or methyl esters, depending on the conditions used. The reaction conditions are mild and generally provide complete conversion in 5–30 min.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/op200118h
