Safe and fast flow synthesis of functionalized oxazoles with molecular oxygen in a microstructured reactor

The synthesis of hydroperoxymethyl oxazoles by oxidation of alkylideneoxazoles with molecular oxygen was implemented in a microstructured reactor for increased safety and larger-scale applications. Elaborate studies on the influence of pressure and temperature were performed, and the apparent activa...

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Main Authors: Bay, Sarah (Author) , Baumeister, Tobias (Author) , Hashmi, A. Stephen K. (Author) , Röder, Thorsten (Author)
Format: Article (Journal)
Language:English
Published: June 13, 2016
In: Organic process research & development
Year: 2016, Volume: 20, Issue: 7, Pages: 1297-1304
ISSN:1520-586X
DOI:10.1021/acs.oprd.6b00118
Online Access:Verlag, Volltext: http://dx.doi.org/10.1021/acs.oprd.6b00118
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Author Notes:Sarah Bay, Tobias Baumeister, A. Stephen K. Hashmi, and Thorsten Röder

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520 |a The synthesis of hydroperoxymethyl oxazoles by oxidation of alkylideneoxazoles with molecular oxygen was implemented in a microstructured reactor for increased safety and larger-scale applications. Elaborate studies on the influence of pressure and temperature were performed, and the apparent activation energy for the oxidation reaction was determined. Elevated temperatures up to 100 °C and pressures up to 18 bar(a) led to a conversion rate of approximately 90% within 4 h of the reaction time, thus displaying the high potential and beneficial effect of using a microreactor setup with liquid recycle loop for this oxidation. The in situ reduction of the generated hydroperoxide functionality shows the capability of this setup for follow-up transformations. 
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