Chloromethylation of Acedianthrone

Abstract

For the synthesis of acedianthrone, in the first place, I investigated the method to get its intermediate, dianthrone-ethane, from anthrone and glyoxal sulfate and succeeded to find the optimum condition. Chloromethylation of acedianthrone was carried out in conc. sulfuric acid with sym-dichlorodimethyl ether, the conditions for chloromethylation were investigated and a bischloromethyl compound was isolated. By the decomposition of this product with chromic acid anthraquinonecarboxylic acid was obtained. The position of chloromethyl group was identified thus. Pyridinium and isothiuronium salts were obtained from the chloromethylated compound, and these dyeing abilities investigated.