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
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 (0
oC) 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, J 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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Keywords: acid chloride, carboxylic acids
