Application of Lanthanoids to Organic Chemistry. Direct Alkoxylation of Anthracene

Abstract

Direct alkoxylation of anthracene with some lower alcohols and ethylene glycol monoalkyl ethers, or monoacetate were carried out in the presence of cerium(IV)tetrakis(trifluoro acetate), and expected alkoxylated anthracene derivatives were obtained.

Synthesis of 9-Anthryl Ethers from trans-9,10-Dihydro-9,10-dimethoxy­anthracene by Acid-Catalyzed Transetherification

“…5 Several methods have been devised to synthesize 9-anthryl ethers, such as, the etherification of 9-anthrone with alcohols under acidic conditions, 6 alkylation via aromatization by phase transfer catalysis, 7 and direct alkoxylation using cerium(IV) tetrakistrifluoroacetate (CTFA). 8 However, these methods are limited, because the starting 9-anthrol is as the minor tautomeric form of the 9-anthrol and 9-anthrone tautomerization. Thus, under the William ether synthetic conditions, 10-alkylated 9-anthrone could be obtained as major product.…”

“…In case of primary alcohols, transetherification yields were 65-68%, which are much higher than previously reported (entries 2-6). 8,9,14 When 2-methoxyethanol was used, transetherification gave the corresponding 9-(2-methoxyethoxy)anthracene (2g) in good yield (73%, entry 7). On the other hand, when 1-bromoethanol was used, we obtained the desired product 2h in only 25% yield (entry 8).…”