81600-36-4Relevant academic research and scientific papers
A novel synthesis of 4-methyl-1,3-dioxolane-4-carbaldehydes by epoxidation of 5-methyl-4H-1,3-dioxins and acid-catalyzed rearrangement
Wattenbach, Carsten,Maurer, Martin,Frauenrath, Herbert
, p. 303 - 306 (1999)
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.
