Selective methoxy ether cleavage of 2,6-dimethoxyphenol followed by a selective acylation

Autor:	Ingo Janser, Ranjith K. Meka, Romy F.J. Janser, Samuel S. Fairbanks, Enoch A. Adogla, Caitlyn M. Vortolomei
Rok vydání:	2011
Předmět:	Catechol Chemistry Fries rearrangement Organic Chemistry Supramolecular chemistry Biochemistry Chloride Article Acylation chemistry.chemical_compound Meta Drug Discovery medicine Organic chemistry Ether cleavage Friedel–Crafts reaction medicine.drug
Zdroj:	Tetrahedron letters. 53(1)
ISSN:	0040-4039
Popis:	A Friedel–Crafts reaction of 2,6-dimethoxyphenol in the presence of aluminum chloride and propanoyl or butanoyl chloride, 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 does not 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::46c4e11cf03d023b62a49f2b12481e11 https://pubmed.ncbi.nlm.nih.gov/22162619 Zobrazit plný text záznamu Full Text from ScienceDirect