Singh, R. P.;Korytnyk, W. published 《Pyridoxine chemistry. VII. Some modifications in the 4-position of pyridoxol》. The research results were published in《Journal of Medicinal Chemistry》 in 1965.Synthetic Route of C8H12ClNO2 The article conveys some information:
cf. preceding abstract Derivatives of I were prepared by treatment of 2,2,8-trimethyl-4H-m-dioxino[4,5-c]pyridine-5-methanol benzoate with HCl. I (R = OH) refluxed with SOCl2 and the residue treated with EtOH produced I (R = Cl). The catalytic (C) hydrogenation of I (R = Cl) afforded I (R = H). I (R = H) refluxed in KOH gave 4-deoxypyridoxine (II). I (R = Cl) stirred with Na2S2O5 produced I (R = SO3H). KCNS refluxed with I (R = Cl) gave I (R = SCN). Similarly, I (R = Cl) stirred with NaHS gave I (R = SH). I (R = H) was as active and I (R = SO3H) one-half as active as II in depressing lymphocyte count in rats fed a pyridoxine deficient diet, while the other reported derivatives were inactive. None of the other compounds inhibited the growth of Saccharomyces carlsbergensis. Cf. Schmidt, and Giesselmann, CA 58, 1429d. The experimental procedure involved many compounds, such as 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride (cas: 148-51-6) .
5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride(cas:148-51-6 Synthetic Route of C8H12ClNO2) is a strong antagonist of vitamin B6. Deoxypyridoxine hydrochloride has been used as an analytical reference standard for the quantification of the analyte in food samples using high performance liquid chromatography.
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