Bulletin of the Chemical Society of Japan p. 433 - 436 (1985)
Update date:2022-08-05
Topics:
Hongo, Chikara
Tohyama, Masanori
Yoshioka, Ryuzoki
Yamada, Shigeki
Chibata, Ichiro
The asymmetric transformation of DL-p-hydroxyphenylglycine was achieved between two enantiomers by a combination of preferential crystallization of desired enantiomer of p-hydroxyphenylglycine o-toluenesulfonate (HPG.o-Ts) and the simultaneous racemization of the antipode.L-HPG.o-TS was easily racemized by heating at 100 deg C in aqueous 95percent (v/v) acetic acid in the presence of small amounts of salicylaldehyde and free DL-HPG.A supersaturated solution of DL-HPG.o-TS placed under such conditions for racemization was seeded with the crystals of D-HPG.o-TS, and added with DL-HPG and o-toluenesulfonic acid in order to provide contonously the supersaturated of DL-HPG.o-TS as a driving force.As a result, 77.2percent of DL-HPG added was transformed to D-isomer.
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