Despite of the fact that resolution is an extremely important process in the pharmaceutical and agrochemical industries, the development of the separation of enantiomers is still based on trial-and-error experiments. In order to compare the different procedures, the resolution of 8-(phenylsulfinyl)-1-naphthoic acid 1 was carried out by chiral organic bases using heat facilitated diastereomeric crystallization, enantioselective liquid–liquid extraction and chiroselective transport. The results give valuable information about the interactions in the racemate/resolving agent/solvent system, which helps with the understanding and development of resolution processes. Diastereomeric crystallization with brucine as a resolving agent afforded enantiomerically pure (−)-1.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry