Continuous Flow Oxidation of Alcohols and Aldehydes Utilizing Bleach and Catalytic Tetrabutylammonium Bromide

Author(s)
Leduc, Andrew B.; Jamison, Timothy F.
Thumbnail
DownloadLeduc Jamison OPRD 2012.pdf (438.1Kb)
PUBLISHER_POLICY
Terms of use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Metadata
Show full item record
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.
Date issued
2011-06
URI
http://hdl.handle.net/1721.1/76284
Department
Massachusetts Institute of Technology. Department of Chemistry
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
ISSN
1083-6160
1520-586X
Collections