A One-Pot Synthesis of Dimethyl 2,3-O-Benzylidene-L-tartrate from L-Tartaric Acid |
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| Authors: | Hoe-Sup Byun Robert Bittman |
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| Institution: | Department of Chemistry and Biochemistry , Queens College of The City University of New York, Flushing , New York, 11367-1597 |
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| Abstract: | An economical one-pot synthesis of (-)-dimethyl 2,3-O-benzylidene-L-tartrate (4R, 5S)-4,5-bis(methoxycarbonyl)-2-phenyl-1,3-dioxolane] and its enantiomer from the corresponding tartaric acids is reported in 83-91% yield. The desired benzylidene tartrate is obtained by reaction of tartaric acid and benzaldehyde (1.5 equiv) in the presence of p-toluenesulfonic acid in methanol followed by the addition of 3 equiv of trimethyl orthoformate, which reacts with the water generated in the reaction. |
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