Glycerol menthonide,
2a, has been prepared from menthone,
1, and glycerol under acidic conditions and has been shown to be mixture of at least 4 isomers. One of the isomers,
2a, has been isolated after conversion to the 4-bromobenzoate,
3a. Methanolysis followed by oxidation with Dess-Martin reagent yielded an aldehyde,
4a. The aldehyde was reacted with phenylmagnesium bromide to yield alcohol
5a.
