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Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones

✍ Scribed by Anthony J. Manny; Staffan Kjelleberg; Naresh Kumar; Rocky de Nys; Roger W. Read; Peter Steinberg

Book ID
104208169
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
902 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

A synthesis of ethyl-, butyl-, hexyl-and dodecyi-substituted fimbrolides from aikyl-substituted levulinic acid derivatives through brominafiou and acid promoted lactonisafion is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the Im~nination conditions and changing acid concentration on product distribution ate discussed. Dibrominatiou proceeds best in CHCI 3 and proceeds in EtOH-free CHCI 3 without the complication of ester formation. Cyclisation occurs with concomitant oxidation in 98-100% H2SO4 but gives highest yields of fimbrofides in 100% H2SO 4. The formation of related beckerclids substances is also described. O 1997

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