Optical Resolution of 1-(3-Methoxyphenyl)ethylamine with Enantiomerically Pure Mandelic Acid, and the Crystal Structure of Less-Soluble Diastereomeric Salt

1993 ◽  
Vol 66 (11) ◽  
pp. 3414-3418 ◽  
Author(s):  
Kenichi Sakai ◽  
Yukihiko Hashimoto ◽  
Kazushi Kinbara ◽  
Kazuhiko Saigo ◽  
Hisamichi Murakami ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Mandelic Acid ◽  
Optical Resolution ◽  
Enantiomerically Pure

Optical Resolution of Mandelic Acid by Complexation with (S)-(+)-Alanine

2002 ◽  
Vol 2002 (9) ◽  
pp. 446-447 ◽  
Author(s):  
Koichi Tanaka ◽  
Takatumi Fukuoka ◽  
Matoo Shiro
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Solid State ◽  
Mandelic Acid ◽  
Optical Resolution ◽  
Hydrogen Bond Network ◽  
Bond Network

Racemic mandelic acid (2) was resolved efficiently by complexation with ( S)-(+)-alanine (1) and the crystal structure of 2:2:1 complex of ( S)-(+)-alanine (1), ( R)-(-)-mandelic acid (2) and H2O was determined characterizing the hydrogen bond network in the solid state.

scholarly journals Microwave-Assisted Synthesis of(±)-Mandelic Acid-d5, Optical Resolution, and Absolute Configuration Determination

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Claudio Bruno ◽  
Giovanni Lentini ◽  
Angelo Lovece ◽  
Maria Maddalena Cavalluzzi ◽  
Alessia Carocci ◽  
...  
Keyword(s):  
Capillary Electrophoresis ◽  
Mandelic Acid ◽  
Optical Resolution ◽  
Racemic Mixture ◽  
Microwave Assisted Synthesis ◽  
Salt Formation ◽  
Microwave Assisted ◽  
Diastereomeric Salts ◽  
Chiral Capillary Electrophoresis ◽  
Resolving Agents

An efficient microwave-assisted synthesis of(±)-mandelic acid-d5was developed. The racemic mixture was resolved by diastereomeric salt formation using 1-phenylethylamine enantiomers as resolving agents. At each step, the resolution process was checked by determining mandelic acid-d5enantiomer ee values directly on fractional crystallized diastereomeric salts by chiral capillary electrophoresis analysis. Highly enriched (−)- and (+)-mandelic acid-d5(95% and 90% ee, resp.) were obtained and their absolute configurations—RandS, respectively—were determined by correlation of the (−)-mandelic acid-d5circular dichroism spectrum to the (R)-mandelic acid one.

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