Benzyl Alcohol → 6-((Benzyloxy)carbonyl)picolinic acid

Participants

Reaction Steps

A mixture of 2,6-pyridinedicarboxylic acid (10 g, 0.06 mol) and benzyl alcohol (68 mL, 0.66 mol) were taken in water (25 mL), and concentrated H2SO4 (3.5 mL) was added. The reaction mixture was refluxed for 10 h and further allowed to stir at room temperature for 24 h. The reaction mixture was concentrated under reduced pressure and the organic product was extracted with CHCl3. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% MeOH in CH2Cl2) to afford 6-((benzyloxy)carbonyl)picolinic acid (4.6 g, yield 30%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.54 (br s, 1H), 8.29-8.24 (m, 2H), 8.20-8.16 (m, 1H), 7.52-7.50 (m, 2H), 7.44-7.36 (m, 3H), 5.43 (s, 2H). MS (ESI) m/z: Calculated for C14H11NO4: 257.07. found: 258.2 (M+H)+.

Provenance & Evidence