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Friedel Crafts cylisation of 3-(1-Pyrenyl)propanoyl chloride; 3,4-dihydro-5H-Benzo[cd]pyren-5-one

SyntheticPage 534
DOI: 10.1039/SP534
Submitted Feb 03, 2012, published Feb 09, 2012
Anish Mistry (a.mistry@warwick.ac.uk)
A contribution from Fox Group, Warwick University


			Reaction Scheme: Friedel Crafts cylisation of 3-(1-Pyrenyl)propanoyl chloride<img src="/images/empty.gif" alt="" />

Chemicals Used

3-(1-Pyrenyl)propanoyl chloride S|P 517
Aluminium Chloride (2 eq, Sigma-Aldrich)
DCM

Procedure

Anhydrous Aluminium Chloride (0.17 g, 1.3 mmol)  was added to a stirring solution of 3-(1-Pyrenyl)propanoyl chloride (0.19 g, 0.65 mmol) in DCM 15 ml) at 0oC under a dinitrogen atmosphere. The reaction was then left for 1 h under a dinitogen atmosphere at room temperature.
The solvent was removed in vacuo, the residue was acidified with HCl (1 M) and then extracted with DCM (3 x 10 ml). The combined extracts were collected and dried over Na2SO4 and the solvent removed in vacuo to produce a yellow/orange crude residue. This was purified by coloumn chromatography using (8:2) chloroform : petroleum ether (40 - 60 oC) to yield dark yellow crystalline solid (25 mg, 15%).

Author's Comments

You should be careful upon addition of HCl as toxic/corrosive gas is evolved.
The end product is susceptible to oxidation over long periods of time.

Data

δH(400MHz, CDCl3) ppm: 3.09 (2H, t, 7.0, CH2), 3.63 (2H, t, J 7.0, CH2), 7.87 (1H, d, J 8, aryl), 7.96 - 8.03 (3H, m, aryl), 8.12 (1H, d, J 8, aryl), 8.20 (1H, d, J 7.5, aryl), 8.28 (1H, d, J 7.5, aryl), 8.74 (1H, s, aryl).

Lead Reference

Preparation, Properties, and Some Chemical Reactions of PhenaIeno [1,9-bc] furan, Gamini Weeratunga, Mona Austrup, and Russell Rodrigo, J. Chem. Soc. Perkin Trans. I, 1988, 3169-3173.

Other References

Mild, Efficient Friedel-Crafts Acylations from Carboxylic Acids Using Cyanuric Chloride and AlCl3, Cyrous O. Kangani and Billy W. Day, Org. Lett., Vol. 10, No. 13, 2008, 2645-2648.

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Get structure file (.cdx, .sk2, .mol)

Keywords: aromatics/arenes, cyclisation

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