Evodone (23). To a suspension of 5 mg (0.05 mmol) of hydroquinone in 20 mL of freshly distilled ethylbenzene in a 25-mL, round-bottomed flask was added 60 mg (0.30 mmol) of acetylenic ketone 22. The resulting solution was refluxed in the absence of light and under an atmosphere of dry N2 for a period of 96 h.The ethylbenzene was then removed under reduced pressure to afford ~70 mg of a dark brown oil. Thick-layer chromatography (40% acetone/petroleum ether, R¡ 0.65) of this material afforded 39 mg (76%) of 23 as a colorless crystalline solid. Recrystallization from MeOH/H20 gave colorless needles, which after sublimation (0.015 mmHg, 25 °C) had a melting point of 70-71 °C (lit.7 mp 73 °C):
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.