Method of producing derivatives of 1,3,5-triarylbenzene and truxene

摘要

A method of producing 1,3,5-triarylbenzenes comprises subjecting a first compound with the formula Ar-C(=O)Me, where Ar is phenyl (optionally substituted with alkyl, chlorine, bromine, iodine or nitro), pyrenyl, fluoroanthenyl, or triphenylenyl, to an aldol condensation reaction using an alkyl orthosilicate of formula Si(OAk)4, where Ak is C1-10 alkyl and an inorganic or organic non-carboxylic acid in an aprotic organic solvent. Another method concerns the production of truxene derivatives by treating a second compound containing a ketone group attached to a cyclopentyl ring fused to a phenyl ring, the method comprising adding Si(OAk)4 and an acid. The phenyl ring of the second compound is optionally substituted by alkyl, chlorine, bromine, iodine, or nitro. The truxene derivatives may be CH2-bridged derivatives of 1,3,5-triarylbenzenes. The first compound may be 2-bromoacetophenone, 2-nitroacetophenone, 2-acetyltriphenylene, 1-aceylpyrene or the indanone of the second compound. The acid may be methanesulphonic acid, chlorosulphonic acid, sulphuric acid, p-toluenesulphonic acid, hydrogen chloride, or trifluoromethanesulphonic acid. The solvent may be methylene chloride, toluene, or chloroform.