Acetic Acid → 3-Hydroxypyridine-2,6-dimethanol

Participants

Reaction Steps

71.1 g (0.75 mol) of 3-hydroxypyridine are dissolved in 300 ml of a 10% aqueous NaOH solution. The combined mixture is brought to 90° C. and then 7×60 ml of a 30% formaldehyde solution are introduced portionwise (5.1 mol). The mixture is left at ambient temperature overnight and then neutralized with CH3COOH. It is concentrated and the residue is taken up in 600 ml of DMF. The insoluble light material is separated. The liquors are acidified with 75 ml 10N HCl. The mixture is concentrated. The residual oil is purified by chromatography on silanized silica with elution with water. Crystals are obtained. w=47 g.

Provenance & Evidence