Sodium Hydroxide → 3,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

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Reaction Steps

30% aqueous sodium hydroxide was added over a solution of crude 2-acetoxymethyl-3,5-dimethyl-4-methoxypyridine prepared from 30.06 g (0.18 mole) of 2,3,5-trimethyl-4-methoxypyridine N-oxide, to pH 13. The mass was stirred for about 3.5 hours at 25°-28° C., with addition of 30% aqueous sodium hydroxide at the appropriate rate to hold the pH to between 11.7 and 13. Once the reaction was terminated (complete disappearance of the band located towards 1700 cm-1) the pH was adjusted to 6.5 with acetic acid, water was added and the mass was extracted with methylene chloride. The solvent was removed by vacuum distillation and finally 2-hydroxymethyl-3,5-dimethyl-4-methoxypyridine was distilled at 142°-145° C. (9 torr.) as a colourless liquid which crystallised on standing. 27.23 g were obtained. Yield 92.4%.

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