2,6-Pyridinedimethanol

5453-67-8

1195-59-1

General procedure for the synthesis of 2,6-pyridinedimethanol from dimethyl pyridine-2,6-dicarboxylate: dimethyl pyridine-2,6-dicarboxylate (9.75 g, 50 mmol) was dissolved in 40 mL of anhydrous ethanol and stirred under ice-bath conditions. Sodium borohydride (7.8 g, 4 eq.) was added in batches over 15 min and the reaction mixture was kept stirring at 0°C for 1 hr. The ice bath was then removed and the reaction mixture was allowed to continue stirring at room temperature for 2 hours. Next, the reaction mixture was placed on a steam bath and heated to reflux for 10 hours. Upon completion of the reaction, the solvent was removed by vacuum distillation. The residue was mixed with 40 mL of acetone and heated on a steam bath for 1 hour, after which the solvent was again removed by vacuum distillation. The resulting residue was mixed with 40 mL of aqueous potassium carbonate and heated on a steam bath for 1 hour, after which the solvent was removed by vacuum distillation. The final residue was dissolved in 100 mL of water and the aqueous solution was continuously extracted with chloroform for 10 h. The final 2,6-pyridinedimethanol was obtained as 6 g (87% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.70 (t, J=7.6 Hz, 1H), 7.20 (d, J=7.7 Hz, 2H), 4.78 (s, 4H).