Ethanol → Ethyl 3-hydroxypicolinate

Participants

Reaction Steps

To a stirred solution of 5.0 g (36 mmol) of 3-hydroxylpicolinic acid in 120 mL ethanol and 40 ml benzene was added 2.0 ml of 98% sulfuric acid. The reaction was refluxed for 40 h. After the solvents were evaporated, the residue was dissolved in 100 ml of water, neutralized with saturated sodium bicarbonate solution and extracted with dichloromethane 3 times. The combined organics were dried over magnesium sulfate, filtered and evaporated in vacuo to afford 3.5 g (58% yield) of the title compound as a brown residue that was used without further purification.

Provenance & Evidence