Water → 1-(11,12-Dihydroxydodecyl)-3,7-dimethylxanthine

Participants

Reaction Steps

A solution of 1-(11-dodecenyl)-3,7-dimethylxanthine, prepared above (4.70 g, 13.6 mmol), 4-methylmorpholine-N-oxide (4.79 g, 40.7 mmol) and potassium osmate dihydrate (52 mg, 0.14 mmol) in acetone/water 1:2 (75 ml) was stirred for 16 hours. Water (50 ml) and sodium sulfite (5 g) were subsequently added to the solution and the resulting reaction mixture stirred for 1 hour. The reaction mixture was extracted with dichloromethane (3×100 ml), dried using magnesium sulfate and the solvent evaporated, resulting in a pale, green solid. Recrystallization from hot ethyl acetate yielded 4.32 g of a white solid, 1-(11,12-dihydroxydodecyl)-3,7-dimethylxanthine (84% yield).

Provenance & Evidence