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Optical resolution by preferential crystallization of 4‐methylpiperidinium hydrogen (RS)‐phenylsuccinate
Author(s) -
Shiraiwa Tadashi,
Ohki Yasunobu,
Sado Yujin,
Miyazaki Hideya,
Kurokawa Hidemoto
Publication year - 1994
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.530060307
Subject(s) - chemistry , crystallization , recrystallization (geology) , hydrochloric acid , solubility , salt (chemistry) , supersaturation , nucleation , dissolution , gibbs free energy , crystallography , inorganic chemistry , organic chemistry , thermodynamics , biology , paleontology , physics
Gibbs energy of racemate formation, binary melting point diagram, and ternary solubility diagram suggested that 4‐piperidinium hydrogen (RS)‐phenylsuccinate [(RS)‐4‐MP salt] exists in a conglomerate. Appropriate conditions were explored on the basis of free energy of critical nucleation in a supersaturated solution to resolve efficiently (RS)‐4‐MP salt by preferential crystallization. Successive preferential crystallization of (RS)‐4‐MP salt in ethanol at 20°C gave (R)‐ and (S)‐4‐MP salts of 90–94% optical purities. Optically pure (R)‐ and (S)‐phenylsuccinic acids were obtained by recrystallization of the (R)‐ and (S)‐4‐MP salts, followed by treatment of the salts purified with hydrochloric acid. © 1994 Wiley‐Liss, Inc.