Zur Formylierung von Hydroxy- und Alkoxyaromaten mit Ameisensäure
Author:
Kantlehner Willi12, Ziegler Georg3, Mezger Jochen3, Sommer Jean4, Louis Benoit4, Sievers Björn3, Ivanov Ivo C.3, Samain Xavier4, Leonhardt Silvia3, Frey Wolfgang5
Affiliation:
1. Institut für Angewandt Forschung, Abteilung Technische Organische Synthesechemie und Katalyseforschung , Hochschule Aalen, Beethovenstr. 1, D-73430 Aalen , Germany 2. Institut für Organische Chemie , Universität Stuttgart , Pfaffenwaldring 55 , 70569 Stuttgart , Germany , Fax: +49(7361)5762250 3. Fakultät Chemie/Organische Chemie, Hochschule Aalen , Beethovenstr. 1, D-73430 Aalen , Germany 4. Laboratoire de Physico-Chimie des Hydrocarbures, Université Louis Pasteur UMR 7513 , 4, rue Blaise Pascal, F-67070 Strasbourg Cedex , France 5. Institut für Organische Chemie, Universität Stuttgart , Pfaffenwaldring 55, 70569 Stuttgart , Germany
Abstract
Abstract
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.
Publisher
Walter de Gruyter GmbH
Subject
General Chemistry
Reference34 articles.
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