Zur Formylierung von Hydroxy- und Alkoxyaromaten mit Ameisensäure

Autor:	Benoit Louis, Ivo C. Ivanov, Björn Sievers, Wolfgang Frey, Jochen Mezger, Jean Sommer, Xavier Samain, Willi Kantlehner, Georg Ziegler, Silvia Leonhardt
Rok vydání:	2019
Předmět:	chemistry.chemical_compound 010405 organic chemistry Chemistry Formic acid General Chemistry 010403 inorganic & nuclear chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences
Zdroj:	Zeitschrift für Naturforschung B. 74:709-732
ISSN:	1865-7117 0932-0776
DOI:	10.1515/znb-2019-0076
Popis:	By treatment of ethers of phenol, resorcinol, 2-napththol, alkylanisoles 10, 13, 15, 17, 20, 22, 24, 28 with formic acid/borontrichloride the aromatic aldehydes 11, 14, 16, 18, 21, 23, 25, 26, 29 can generally be prepared in low yields. The formylation reactions proceed between −20 and −10°C within 20 min in 1,2-dichloroethane, chlorobenzene, or methylene chloride as solvents when formic acid and borontrichloride are used in excess [molar ratio of aromatic compound to HCOOH to BCl3 = 1:1.2–1.7:1.6–1.8]. The more strongly activated 3,5-dimethoxyphenol (33) is formylated by formic acid/borontrichloride to give the aldehyde 34 with an acceptable yield. The reactions of resorcinol dimethylether with formic acid in the presence of super acids (mainly trifluormethansulfonic acid) in chlorobenzene or nitromethane deliver the aldehyde 21 only in small amounts.
Databáze:	OpenAIRE
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