The synthesis and hydrolysis of dimethyl acetals catalyzed by sulfated metal oxides. An efficient method for protecting carbonyl groups

• Published in: Catalysis letters 2001-05, Vol.73 (2-4), p.121-125
• Main Authors: LIN, Chiu-Hsun, LIN, Shawn D, YANG, Yi-Hung, LIN, Tsung-Po
• Format: Article
• Language: English
• Subjects: Acetals; Acetone; Aldehydes; Aluminum oxide; Carbonyl compounds; Carbonyl groups; Carbonyls; Catalysis; Catalysts; Catalysts: preparations and properties; Chemical synthesis; Chemistry; Dimethyl acetals; Exact sciences and technology; General and physical chemistry; Hafnium oxide; Hydrolysis; Ketones; Metal oxides; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Tin dioxide; Titanium dioxide; Zirconium dioxide
• ISSN: 1011-372X; 1572-879X
• DOI: 10.1023/A:1016681422187

Sulfated metal oxides including SO42−/ZrO2, SO42−/TiO2, SO42−/HfO2, SO42−/Fe2O3, SO42−/SnO2, and SO42−/Al2O3 were highly efficient catalysts for the reaction of aldehydes and ketones with trimethyl orthoformate producing dimethyl acetals under mild reaction conditions. At room temperature, dimethyl acetal yields of 83–100% were obtained for the five carbonyl compounds chosen. These mesoporous solid acids also effectively catalyzed the hydrolysis of dimethyl acetal to regenerate the original carbonyl compounds in aqueous acetone. They not only provided an effective method for synthesizing dimethyl acetals of larger molecular size but also acted as a versatile catalyst for protecting and deprotecting carbonyl groups during organic synthesis.