| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 67889 | Journal of Molecular Catalysis A: Chemical | 2007 | 8 Pages |
Shape selective acetylation of 4,4′-dimethylbiphenyl using anhydrous aluminum chloride as catalyst is an effective route for the production of mono- and di-acetyl-4,4′-dimethylbiphenyl. Preparations, characterization and a catalytic study of the Friedel-Crafts acetylation of 4,4′-dimethylbiphenyl, involving use of the Perrier addition procedure are carried out in a range of solvents and under a variety of experimental conditions. The obtained ketones are isolated and identified by various physico-chemical techniques. Mono acetylation of 4,4′-dimethylbiphenyl afforded a mixture of two isomeric acetyl dimethylbiphenyls. In chloroalkane or carbon disulfide solvent, the yields of isomers were in the order: 2 -> 3-; in nitromethane 3-isomer predominated. On the other hand diacetylation of the hydrocarbon gave only the 2,3′-diacetyl isomer. The mono- and di-ketones are converted to the corresponding carboxylic acids. 2-Acetyl-4,4′-dimethylbiphenyl was prepared by indirect multi-step synthetic routes. 3-D molecular modelling supports the positional assignment of the acetyl group with the results obtained from the electronic spectra.
Graphical abstractShape selective acetylation of 4,4′-dimethylbiphenyl (DMBPh) with acetyl chloride using aluminum chloride anhydrous as catalyst is an effective route for the production of mono- and di-acetyl-isomers. Systematic study of the catalytic Friedel-Crafts acetylation of DMBPh was carried out in a range of solvents and under a variety of experimental conditions. The obtained ketones were converted to the corresponding carboxylic acids. 2-acteyl-4,4′-dimethylbiphenyl was prepared by indirect stepwise synthetic route. 3-D molecular modeling supports the positional assignment of the acetyl group with the results obtained from the electronic spectra.Figure optionsDownload full-size imageDownload as PowerPoint slide
