A Novel Synthesis of 4-Methyl-1,3-Dioxolane-4-Carbaldehydes by Epoxidation of 5-Methyl-4H-1,3-Dioxins and Acid-Catalyzed Rearrangement
- 1 March 1999
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1999 (3) , 303-306
- https://doi.org/10.1055/s-1999-2601
Abstract
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.Keywords
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