Optical resolution of (±)‐Threo‐9,10,16‐trihydroxy hexadecanoic acid using (−)brucine

Optical resolution of (±)‐Threo‐9,10,16‐trihydroxy hexadecanoic acid using (−)brucine

The optical resolution of (±)threo‐9,10,16‐trihydroxy hexadecanoic acid was achieved by fractional crystallization using (−)brucine. Formation of an estolide during decomposition of the (−)brucine complex was observed to interfere with the separation of the optically pure material. This was correcte...

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Veröffentlicht in:Journal of the American Oil Chemists' Society 1998-10, Vol.75 (10), p.1461-1463
Hauptverfasser: Malkar, Navdeep B., Kumar, V. G.
Format: Artikel
Sprache:eng
Schlagworte:
(±)threo‐aleuritic acid
(−)Brucine
Aliphatic compounds
Chemistry
chiral NMR shift reagent
Crystallization
estolide
Exact sciences and technology
Fractional crystallization
Neutralization
NMR
Nuclear magnetic resonance
optical resolution
Organic chemistry
Palmitic acid
Preparations and properties
Reagents
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Beschreibung
Zusammenfassung:The optical resolution of (±)threo‐9,10,16‐trihydroxy hexadecanoic acid was achieved by fractional crystallization using (−)brucine. Formation of an estolide during decomposition of the (−)brucine complex was observed to interfere with the separation of the optically pure material. This was corrected by converting the estolide to (+)‐threo‐9,10,16‐trihydroxy hexadecanoic acid via alcoholic alkaline hydrolysis followed by neutralization. Enantiomeric purity was determined by chiral lanthanide nuclear magnetic resonance shift reagent.
ISSN:0003-021X
1558-9331
DOI:10.1007/s11746-998-0202-9