The chrysanthemumcarboxylic acids. IV.—optical resolution of the chrysanthemic acids
- 1 April 1952
- journal article
- research article
- Published by Wiley in Journal of the Science of Food and Agriculture
- Vol. 3 (4) , 189-192
- https://doi.org/10.1002/jsfa.2740030412
Abstract
Resolution of (±)‐trans‐chrysanthemic acid by fractional crystallization of the quinine salt yields the pure (‐)‐trans‐acid quinine salt, decomposed by hydrochloric acid to optically pure (‐)‐trans‐chrysanthemic acid. Conversion of the impure (+)‐trans‐acid into the (‐)‐α‐phenylethylamine salt and fractional crystallization yields the pure (+)‐trans‐acid (‐)‐α‐phenylethylamine salt, decomposed to optically pure (+)‐trans‐chrysanthemic acid. This completes the total synthesis of chrysanthemum‐monocarboxylic acid.Resolution of (±)‐cis‐chrysanthemic acid as the quinine salt yields the pure (+)‐cis‐acid quinine salt, decomposed to the optically pure crystalline (+)‐cis‐chrysanthemic acid. Conversion of the impure (‐)‐cis‐acid into the (+)‐α‐phenylethylamine salt and fractional crystallization yields the pure (‐)‐cis‐acid (+)‐a‐phenylethylamine salt, decomposed to the optically pure crystalline (‐)‐cis‐chrysanthemic acid.Keywords
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