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Efficient Preparation of (R) ‐2‐chloromandelic Acid Via a Recycle Process of Resolution
Author(s) -
Hu Yu,
Wu Chang,
Wu XueYing,
Li ShaoLei,
Sun XiaoXia,
Tang ZeBiao
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22427
Subject(s) - chemistry , racemization , resolution (logic) , carbanion , tartaric acid , process (computing) , sodium hydroxide , combinatorial chemistry , stereochemistry , organic chemistry , artificial intelligence , computer science , citric acid , operating system
Abstract Efficient preparation of (R) ‐2‐chloromandelic acid (R)-1 based on a recycle process of resolution is described. In the process, the desired (R)-1 was obtained by coordination‐mediated resolution with D ‐O,O'‐di‐(p‐toluoyl)‐tartaric acid in the presence of Ca 2+ . Meanwhile, the undesired (S)-1 could be racemized in the presence of sodium hydroxide and the product was suitable for further resolution. A carbanion mechanism for the racemization of (S)-1 is proposed. Chirality 27:281–285, 2015 . © 2015 Wiley Periodicals, Inc.