Ethyl isonicotinate → 3-Pyridinemethanol

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In Mosher, Harry S. et al., Journal Of American Chemical Society, 73 Oct.(1951) pp.4925-4927, 3-chloromethyl and 4-chloromethyl pyridinium hydrochloride was prepared by first reducing ethyl nicotinate and ethyl isonicotinate with lithium aluminum hydride in anhydrous ether to produce 3-hydroxymethyl pyridine and 4-hydroxymethyl pyridine respectively. The resulting liquid 3-hydroxymethyl pyridine was separated from the distillate by converting to the hydrochloride. The 3- and 4-hydroxymethyl pyridine hydrochloride were added to a substantial excess amount of thionyl chloride and then refluxed followed by the addition of benzene to precipitate out the 3- and 4-chloromethyl pyridine hydrochloride, respectively. Although the resulting 3-chloromethyl pyridine hydrochloride compound appears to be very pure, it apparently exists as a fluffy dusty powder which is difficult to process on a large scale basis.

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