Analysis by RP-HPLC and Purification by RP-SPE of the C-Tetra(p-hydroxyphenyl)resorcinolarene Crown and Chair Stereoisomers

• Published in: Journal of analytical methods in chemistry Vol. 2019; no. 2019; pp. 1 - 6
• Main Authors: Castillo-Aguirre, Alver A., Maldonado, Mauricio, Rivera-Monroy, Zuly J.
• Format: Journal Article
• Language: English
• Published: Cairo, Egypt Hindawi Publishing Corporation 01.01.2019; Hindawi; Hindawi Limited; Wiley
• Subjects: Alcohol; Benzaldehyde; Carbon 13; Chemistry; Decomposition; Ethanol; High performance liquid chromatography; Isomers; Methods; NMR; Nuclear magnetic resonance; Octol (explosive); Organic chemistry; Separation; Solid phases; Solvents
• ISSN: 2090-8865; 2090-8873
• DOI: 10.1155/2019/2051282

A method for the separation of stereoisomer mixture of the octol C-tetra(p-hydroxyphenyl)calix[4]resorcinarene that was obtained by an acid cyclocondensation reaction between resorcinol and benzaldehyde is reported in this paper. A crude product from octol formation reaction was analyzed by reverse-phase high-performance liquid chromatography (RP-HPLC), and two well-resolved signals corresponding to the crown and chair isomers were found. A reverse phase in solid-phase extraction (RP-SPE) protocol allowed the separation of the two stereoisomers with high purity of each isomer. Finally, the crude and purified stereoisomers were characterized by using FT-IR, 1H-NMR, and 13C-NMR techniques, confirming the chemical identity of the two isomers and the efficiency in the separation process.