176505-14-9Relevant academic research and scientific papers
Syntheses of anthracenones. 3. Revised preparative route to 10-Benzoyl-1,8-dihydroxy-9(10H)-anthracenones
Prinz, Helge,Wiegrebe, Wolfgang,Müller, Klaus
, p. 2861 - 2864 (1996)
The acylation of anthralin (1,8-dihydroxy-9(10H)-anthracenone) with acetylsalicylic acid chloride in toluene and collidine was found to give the O-acylated product, rather than 10-(acetylsalicyl)-anthralin. A procedure is described for benzoylation of anthralin in the 10-position which involves reaction of 1,8-diacetoxy-9(10H)-anthracenone with benzoyl chloride and sodium hydride in THF followed by hydrolysis of an intermediate enol ester. Furthermore, when benzoyl chloride and DMF were used for the acylation of anthralin, a Vilsmeier-type reaction was observed leading to a novel enamine derivative of anthralin which was hydrolyzed or benzoylated to an enol or enol ester, respectively.
