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Synlett 2010(13): 2037-2040  
DOI: 10.1055/s-0030-1258534
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© Georg Thieme Verlag Stuttgart ˙ New York

Microwave- or Microreactor-Assisted Conversion of Furfuryl Alcohols into 4-Hydroxy-2-cyclopentenones

Kathrin Ulbrich, Peter Kreitmeier, Oliver Reiser*
Institut für Organische Chemie der Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany
Fax: +49(941)9434121; e-Mail: oliver.reiser@chemie.uni-regensburg.de;
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Publication History

Received 14 June 2010
Publication Date:
28 July 2010 (online)

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Abstract

The conversion of a variety of furfuryl alcohols, derived from renewable non edible resources such as bran, into 4-hydroxy-2-cyclopentenones was accomplished using microwave irradiation. In subcritical water (220 ˚C, 15.5 bar) without the need for any catalyst the reaction proceeds approximately two orders of magnitude faster with up to twice the yield compared to methods previously reported that apply conventional heating techniques. For the parent furfuryl alcohol the process could be transferred to a microreactor, allowing the synthesis of 4-hydroxy-2-cyclopentenone in a continuous flow system on multigram scale.

Key words

green chemistry - organic synthesis in water - microwave chemistry - carbohydrates - biomass - furfuryl alcohol

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10

Irradiation of pure water at 300 W, a maximum temperature of 180 ˚C and 9 bar of pressure is reached.