Hydrochloric Acid → 6-Methyl-2-pyridylmethanol

2-Acetoxymethyl-6-methylpyridine (5 g) was added to saturated hydrochloric acid in methanol (250 ml, prepared by adding 25 ml of acetyl chloride to 225 ml of methanol). The reaction mixture was stirred at room temperature for 18 hours. The solvent was removed under vacuum and the residue was dissolved in dichloromethane (100 ml) and washed with 2N sodium hydroxide solution (3×50 ml). The combined organic layers were washed with brine (1×200 ml), then dried (MgSO4), filtered and evaporated to give the required product as an oil (2.6 g). 1H NMR (250 MHz, CDCl3) δ 2.54 (3H, s), 3.80 (1H, bs), 4.72 (2H, s), 7.04 (2H, d, J=7.7Hz), 7.57 (1H, t, J=7.7Hz).

1. customThe solvent was removed under vacuum
2. dissolutionthe residue was dissolved in dichloromethane (100 ml)
3. washwashed with 2N sodium hydroxide solution (3×50 ml)
4. washThe combined organic layers were washed with brine (1×200 ml)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customevaporated

ORD record

ord-55e5b9c5717b4ade9770157e506a096b

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06255305B1