Synthesis of 3-acetyl-6-(o-methyl benzoyl)-
Received: 4 September 2009 / Accepted: 13 January 2010 / Published online: 11 June 2010
Ó Springer Science+Business Media B.V. 2010
Abstract 3-Acetyl-6-(o-methyl benzoyl)-N-ethylcarbazole was prepared through
successive o-methyl benzoylation and acetylation of N-ethylcarbazole in one pot.
The overall yield was 85.6% and the structure was conﬁrmed by
C-NMR. A preliminary investigation had also been carried out on the mechanism
of the o-methyl benzoylation of N-ethylcarbazole.
Keywords 3-Acetyl-6-(o-methyl benzoyl)-N-ethylcarbazole Á Acylation Á
Carbazole and its derivatives had been widely used in optical materials for their
huge conjugated systems and active intramolecular electron transfer [1, 2].
Recently, with the further research of two-photon chemistry, more and more
people focused their research on the synthesis of new carbazole derivatives with
longer conjugated chain, which was in favor of larger two-photon absorption cross-
section and stronger two-photon property .
Herein, 3-acetyl-6-(o-methyl benzoyl)-N-ethylcarbazole, a new carbazole deriv-
ative with special D–p–D structure, was synthesized through two successive
different acylation of N-ethylcarbazole, as sketched in Scheme 1. In this product,
the N atom of carbazole was linked with an alkyl chain to increase the electron
L. Gong Á C. Qian (&) Á X. Chen
Department of Chemical Engineering, Zhejiang University,
Hangzhou 310027, People’s Republic of China
Engineering Department, ShanghaiChem Engineering Incorporation,
Shanghai 200235, People’s Republic of China
Res Chem Intermed (2010) 36:383–387