Safety of (2S)-(+)-3-Chloropropane-1,2-diol. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: (2S)-(+)-3-Chloropropane-1,2-diol, is researched, Molecular C3H7ClO2, CAS is 60827-45-4, about Stereoselective crystallization of 3-(2,6-dimethylphenoxy)propane-1,2-diol: preparation of the single-enantiomer drug mexiletine.
Racemic 3-(2,6-dimethylphenoxy)propane-1,2-diol 8 undergoes spontaneous resolution upon crystallization This fact is confirmed by the m.p. inspection, vibration spectra and X-ray single crystal diffraction of racemic and scalemic crystalline samples of 8. Racemic 8 has been effectively resolved by a preferential crystallization procedure into (S)- and (R)-enantiomers with ee of approx. 90%. The enantiomeric purity of (S)- and (R)-8 could be increased to ee >99% through simple recrystallization Nonracemic diols 8 were converted into nonracemic 1,2-epoxy-3-(2,6-dimethylphenoxy)propanes (S)- and (R)-7 with ee 98% via Mitsunobu reaction. The reaction proceeded without loss of enantiomeric purity, and the initial configuration of the stereogenic center was conserved. Enantiopure epoxides 7 were converted into nonracemic 1-(2,6-dimethylphenoxy)propan-2-ols 2, which are valuable intermediates in single-enantiomer mexiletine synthesis.
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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com