Acetone → 2,6-Di-tert-butylisonicotinic acid

Participants

Reaction Steps

Jone's reagent was added dropwise to a solution of 4-hydroxymethyl-2,6-di-yt-butylpyridine (Compound B3, 302 mg, 1.37 mmol) in 5 ml of acetone until the solution changed color from light yellow to orange (55 drops of Jone's reagent were consumed). After 5 minutes 2 ml of isopropanol were added to the reaction mixture, and a green precipitate of Cr3+ salt was formed. The precipitate was removed by filtration and the solution was diluted with ethyl acetate, then washed with brine, water and dried over MgSO4. After filtration, the solvent was removed to give the desired product as a white solid (227 mg). 1H NMR δ 7.71 (s, 2H), 1.34 (s, 18H).

Provenance & Evidence