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The chrysanthemumcarboxylic acids. IV.—optical resolution of the chrysanthemic acids
Author(s) -
Campbell Ishbel G. M.,
Harper S. H.
Publication year - 1952
Publication title -
journal of the science of food and agriculture
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.782
H-Index - 142
eISSN - 1097-0010
pISSN - 0022-5142
DOI - 10.1002/jsfa.2740030412
Subject(s) - salt (chemistry) , hydrochloric acid , fractional crystallization (geology) , chemistry , crystallization , resolution (logic) , double salt , organic chemistry , geochemistry , artificial intelligence , basalt , computer science , geology
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.