Application In Synthesis of 2-Hydroxy-2-(4-propoxyphenyl)acetic acidOn October 31, 2021 ,《Enantioseparation of mandelic acid and substituted derivatives by high-performance liquid chromatography with hydroxypropyl-β-cyclodextrin as chiral mobile additive and evaluation of inclusion complexes by molecular dynamics》 appeared in Chirality. The author of the article were Shi, Jie-Hua; Lin, Zhen-Yi; Kou, Song-Bo; Wang, Bao-Li; Jiang, Shao-Liang. The article conveys some information:
The enantioseparation and resolution mechanism of mandelic acid (MA), 4-methoxymandelic acid (MMA), and 4-propoxymandelic acid (PMA) were investigated by reversed-phase high-performance liquid chromatog. (HPLC) with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) as a chiral mobile-phase additive and mol. dynamics simulation. The suitable chromatog. conditions for the enantioseparation of MA, MMA, and PMA were obtained. Under the selected chromatog. conditions, these enantiomers could achieve baseline separation The results of thermodn. parameter anal. revealed that the main driven forces for the enantioseparation of MA, MMA, and PMA could be van der Waals forces and hydrogen-bonding interactions and the chromatog. retention of these chiral compounds was an enthalpy-driven process. The results of the mol. simulation revealed that their chiral resolution mechanism on HP-β-CD was responsible for the formation of inclusion complexes of enantiomers with HP-β-CD with different conformations and binding energies. And the binding energy of HP-β-CD with (S)-isomer was larger than that with (R)-isomer, which is consistent with the exptl. results of the first elution of (S)-isomer. Addnl., it is also confirmed that the interaction energies included the van der Waals energy (ΔEvdw), electrostatic energy (ΔEelec), polar solvation energy, and SASA energy (ΔEsasa), and the separation factor (α) was closely connected with the disparity in the binding energies of optical isomers and HP-β-CD complexes. Meanwhile, from mol. dynamics simulation, it can be found that the Δ(ΔEbinding), (Δ(ΔEbinding) = ΔEbinding,R – ΔEbinding,S) value was in order of MA-HP-β-CD complex > MMA-HP-β-CD complex > PMA-HP-β-CD complex, which was consistent with the order of Δ(ΔG) values obtained from van′t Hoff plot. This indicated that the mol. dynamics simulation has predictive function for chiral resolution2-Hydroxy-2-(4-propoxyphenyl)acetic acid(cas: 79694-16-9Application In Synthesis of 2-Hydroxy-2-(4-propoxyphenyl)acetic acid) was used in this study.
2-Hydroxy-2-(4-propoxyphenyl)acetic acid(cas: 79694-16-9) belongs to ethers.Application In Synthesis of 2-Hydroxy-2-(4-propoxyphenyl)acetic acidAlthough ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly.
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem