Hydrogen Peroxide → Picolinic acid

Participants

Reaction Steps

Ethyl pyruvate (0.9-3 eq.) was stirred and cooled (−20-+0ℑ C.) and hydrogen peroxide (30-35%, 0.9-3 eq) was added dropwise. This solution and a solution of Iron sulfate heptahydrate (0.9-3 eq.) in water (1-5 vol.) were then slowly and simultaneously added dropwise into a stirred solution of 4-Chloropyridine (1 eq) in water (1-5 vol.) and conc. H2SO4 (1-4 eq.) and Toluene (0-20 vol.), keeping the temperature below 25ℑ C. The mixture was then stirred at room temperature until the reaction is judged complete. The mixture was poured into ice cold NaOH (10%) solution. Toluene (2-5 vol.) was added (If not already present), the layers were separated. The toluene layer was washed with 0.5N HCl solution and evaporated to yield the crude 2-Pyridinecarboxylic acid, 4-chloro-3,5-dimethyl-, ethyl ester in over 90% yield based on the consumed starting material and over 50% isolated yield.

Provenance & Evidence