pTSA-catalyzed condensation of xylenols and aldehydes under solvent-free conditions: One-pot synthesis of 9H-xanthene or bisphenol derivatives

• Published in: Comptes rendus. Chimie Vol. 16; no. 11; pp. 1035 - 1041
• Main Authors: Mobinikhaledi, Akbar, Moghanian, Hassan, Deinavizadeh, Maryam
• Format: Journal Article
• Language: English
• Published: PARIS Elsevier SAS 01.11.2013; Elsevier
• Subjects: 9H-xanthene; Bisphenol; Catalysis; Chemistry; Chemistry, Multidisciplinary; Exact sciences and technology; General and physical chemistry; One-pot; Physical Sciences; pTSA; Science & Technology; Solvent-free; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; One-pot; 9H-xanthene; Solvent-free; pTSA; Bisphenol; ORGANIC-SYNTHESIS; SUBSTITUTION; DYES; QUINONE METHIDES; XANTHENE; PHENOLS; FACILE; EFFICIENCY; One pot reaction; Catalytic reaction; Xanthene derivatives; Solvent free reaction; Green chemistry; Aldehyde; Condensation
• ISSN: 1631-0748; 1878-1543; 1878-1543
• DOI: 10.1016/j.crci.2013.03.008

A simple and efficient procedure for the synthesis of 9H-xanthene or bisphenol derivatives has been developed by one-pot condensation of xylenols with aromatic aldehydes in the presence of p-toluenesulfonic acid (pTSA) as a catalyst under solvent-free conditions at 100°C. It is noteworthy that the condensation reaction of 3,5-xylenol with aldehydes produces 9H-xanthene derivatives, while the reaction with other xylenols leads to the corresponding bisphenol derivatives. Different types of aromatic aldehydes are used in the reaction and in every case the products were obtained in good to excellent yields. The structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR and CHN data.