Selective methoxy ether cleavage of 2,6-dimethoxyphenol followed by a selective acylation |
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Authors: | Adogla Enoch A Janser Romy F J Fairbanks Samuel S Vortolomei Caitlyn M Meka Ranjith K Janser Ingo |
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Affiliation: | Laboratory of Organic Synthesis, Catalysis & Biochemistry (LOSCB), Department of Chemistry, New Mexico Institute of Mining and Technology, 801 Leroy Place, Socorro, NM 87801, USA. |
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Abstract: | A Friedel-Crafts reaction of 2,6-dimethoxyphenol in the presence of aluminum chloride and propanoyl or butanoyl chlorid, respectively, lead, at elevated temperatures, to a selective cleavage of one of the methoxy groups followed by a selective acylation of the meta position with respect to the phenolic hydroxyl group. Under the same reaction conditions 2-methoxyphenol doesn't get demethylated; a mechanism to account for these findings is proposed. This reaction gives access to a variety of ortho-acylated catechols. Substituted catechols are widely used in supramolecular chemistry and are precursors of pesticides, flavors and fragrances. Additionally, catechol moieties are found in various natural products. |
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