Monday, June 30, 2008
Emerald Grand Ballroom (Sheraton Burlington Hotel and Conference Center)
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Preparation of Derivatives of An Isomer of Glycerol Menthonide

Amber McCloskey and Anthony J. Kiessling. Mansfield University, Mansfield, PA

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.