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Synlett 1998; 1998(10): 1063-1064
DOI: 10.1055/s-1998-1893
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Convenient O-Methylation of Phenols with Dimethyl Carbonate

Youngmin Lee* , Isao Shimizu
  • *Department of Applied Chemistry, Waseda University, Okubo 3-4-1, Shinjuku-ku, Tokyo 169-8555, Japan
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Publication Date:
31 December 2000 (online)

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Reaction of phenols in dimethyl carbonate in the presence of cesium carbonate at 120-160 °C gave aryl methyl ethers in good yields, whereas the reaction of aliphatic alcohols gave the corresponding alkyl carbonates. This method provides a useful synthetic method for preparation of various aryl methyl ethers without using toxic methyl iodide or dimethyl sulfate. O-Methylation of the aromatic hydroxy group of estradiol was carried out in 2 steps without protection of the alcoholic hydroxy group in the same molecule.

dimethyl carbonate - cesium carbonate - aryl methyl ether - mycophenolic acid - estradiol