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Chlorination of a carboxylic acid; 3-(1-Pyrenyl)propanoyl chloride

SyntheticPage 517
DOI: 10.1039/SP517
Submitted Oct 28, 2011, published Nov 27, 2011
Anish Mistry (a.mistry@warwick.ac.uk)
A contribution from Fox Group, Warwick University


			Reaction Scheme: <img src="/images/empty.gif" alt="" />Chlorination of a carboxylic acid<img src="/images/empty.gif" alt="" />

Chemicals Used

3-(1-Pyrenyl)propionic acid (prepared)
Thionyl Chloride (1 equiv, Fluka)
DMF (two drops)
DCM

Procedure

3-(1-Pyrenyl)propionic acid (0.1 g, 0.36 mmol) was dissolved in DCM (15 ml)  with stirring and placed in an ice bath (0oC) under a dinitrogen atmosphere. Thionyl chloride (0.026 ml, 0.36 mmol) was then added carefully and thereafter DMF (two drops). The reaction was left in the inert atmosphere for an hour at room temperature. The solvent was removed in vacuo and an orange crystalline solid is formed in high yield (96%).

Author's Comments

When concentrating solution in vacuo make sure it is in a fume hood due to toxic gases expelled.

Data

δH(400MHz, CDCl3) ppm: 3.44 (2H, t, 8, 7.5, CH2), 3.77 (2H, t, J 8, 7.5, CH2), 7.89 (1H, d, J 8, aryl), 7.99 - 8.23 (8H, m, aryl).


Lead Reference

Asymmetric synthesis of allylic secondary alcohols: a new general approach for the preparation of α-amino acids, Lorna J.Drummond, Andrew Sutherland, Tetrahedron, 2010, 66, 5349-5356 http://dx.doi.org/10.1016/j.tet.2010.05.066

 

Other References

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 http://dx.doi.org/10.1039/p19880003169

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

Keywords: acid chloride, carboxylic acids

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