Synthesis of hydroxymethylpyridines from pyridinealdehydes was written by Leitis, L.;Shimanskaya, M. V.. And the article was included in Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) in 1980.Electric Literature of C7H9NO This article mentions the following:
2-, 3- And 4-hydroxymethylpyridines, 6-methyl-2-hydroxymethyl and 2,6-bis(hydroxymethyl)pyridine were prepared in 41.0-90.5% yield by reduction of the corresponding aldehydes with NaBH4. The reactivity of the aldehydes decreased in the following order: 2,6-pyridinedicarboxaldehyde > 6-methyl-2-pyridinecarboxaldehyde > 4-pyridinecarboxaldehyde > 2-pyridinecarboxaldehyde > 3-pyridinecarboxaldehyde. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0Electric Literature of C7H9NO).
6-Methyl-2-pyridinemethanol (cas: 1122-71-0) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Electric Literature of C7H9NO
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts