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Synlett 1999; 1999(3): 303-306
DOI: 10.1055/s-1999-2601
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A Novel Synthesis of 4-Methyl-1,3-Dioxolane-4-Carbaldehydes by Epoxidation of 5-Methyl-4H-1,3-Dioxins and Acid-Catalyzed Rearrangement

Carsten Wattenbach* , Martin Maurer, Herbert Frauenrath
  • *Universität Gh Kassel, Fachbereich 19 - Biologie/Chemie, Heinrich-Plett-Straße 40, D-34109 Kassel, Germany; Fax +49(5 61)80 44 69; E-mail: frauenra@hrz.uni-kassel.de
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Publikationsdatum:
31. Dezember 1999 (online)

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A straightforward procedure for the synthesis of 4-methyl-1,3-dioxolane-4-carbaldehydes 2 is reported. The new procedure involves m-CPBA oxidation of 5-methyl-4H-1,3-dioxins 5 in dichloromethane to give (4-(m-chlorobenzoyloxy)-5-hydroxy-5-methyl-1,3-dioxanes 6 and acid-catalyzed rearrangement of 6 to carbaldehydes 2. By using commercially available m-CPBA the oxidation and rearrangement can be carried out as a one-pot reaction. The procedure is also applicable to 4H-1,3-dioxins. Oxidation of 5 in methanol led to 4-methoxy-5-hydroxy-1,3-dioxanes 7, which did not undergo acid-catalyzed rearrangement.

1,3-dioxolane-4-carbaldehydes - vinyl acetals - 4H-1,3-dioxins - m-CPBA oxidation - rearrangement