Ammonium peroxodisulfate

Bislawsone (BL) was synthesized from lawsone (LS) (Tokyo Chemical Industry >98.0%) via reaction with ammonium peroxodisulfate (Tokyo Chemical Industry >99.0%) according to procedures described by Inagaki et al. (Fig. 1).^{23 (link)} 100 mg (0.289 mmol) of BL was then dissolved in 10 mL of anhydrous methanol (Acros Organics 99.8%). 12 mg (1.73 mmol) of Li metal (Sigma Aldrich 99%), preserved in mineral oil (Spectrum Chemical), was then briefly rinsed with a few drops of diethyl ether (Fisher Scientific >99.0%) to remove excess oil and added to the methanol solution of BL. Upon addition of Li, the solution changed in color from bright yellow to dark red. This solution was stirred at room temperature for 20 min and then filtered under vacuum to remove any excess metal or metal oxide. The supernatant solution was then collected from the filtration flask and the solvent was removed under vacuum. The product was then re-dissolved in a very minimal amount of methanol and filtered again. This time the precipitate was washed with diethyl ether and collected to yield 57 mg (57% yield) of lithiated bislawsone (Li-BL) as a dark red solid.