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Synthesis 2009(10): 1703-1707  
DOI: 10.1055/s-0028-1088073
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Keun Sam Janga, Hee Young Shina, Dae Yoon Chi*b
a Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Korea
b Department of Chemistry, Sogang University, 1 Shinsudong Mapogu, Seoul 121-742, Korea
Fax: +82(2)7010967; e-Mail: dychi@sogang.ac.kr;
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Publication History

Received 9 December 2008
Publication Date:
30 April 2009 (online)

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Abstract

During a study of electrophilic aromatic addition reactions (Ad E Ar) to anthracene, anthryl ethers at the C9-position of anthracene were obtained as the major products when trans-9,10-dihydro-9,10-dimethoxyanthracene was reacted (10 minutes at 75 ˚C) with various alcohols. 9-Anthryl ethers with primary, secondary, cyclic alcohols, and polyethylene glycol (PEG) were isolated in 47-73% yields under optimized conditions. It is hoped that the devised method offers a new synthetic route for the preparation of anthryl ethers via the acid-catalyzed transetherification of trans-9,10-dihydro-9,10-dimethoxyanthracene with various alcohols.

Key words

transetherification - anthryl ethers - trans-9,10-dihydro-9,10-dimethoxyanthracene