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An efficient TiCl4-catalysed method for the synthesis of para-substituted aromatic aldehydes

Posted on 13. October, 2015.

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A para-substituted aromatic aldehyde is an important substructure in both natural products and therapeutic agents. 

Cyclamen aldehyde, a typical para-substituted aromatic aldehyde, is often used as an intermediate in efficient syntheses of various compounds such as Sulindac analogues, α- and β-amino acids and β-lactams, bisabolane sesquiterpenes and tricyclic steroid precursors. It is also used as a surrogate for lily aldehyde, which is frequently used in detergents and soaps.
 
This paper presents an efficient and highly selective synthesis of para-substituted aromatic aldehydes has been achieved by TiCl4-catalysed Friedel–Crafts alkylation of monosubstituted benzenes with methacrolein diacetyl acetal.

Authors: Chenfeng Zhoua,b and Weike Sua*
 
aCollaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P.R. China
bCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P.R. China


Keywords: TiCl4, Friedel–Crafts alkylation, aromatic aldehydes


Read the full paper in Journal of Chemical Research, Volume 39, Number 10, Month 2015, pp. 555-616, pp. 555-557.