Abstract
Racemic 2-iodomandelic acid 1 was synthesized from commercially available 2-iodobenzoic acid 2. Acyl chloride 3 was reacted with diethyl malonate, then the formed diester was hydrolysed and decarboxylated in a one-pot reaction. The obtained 2-iodoacetophenone 4 was reacted with bromine and the dibromoacetophenone derivative 5 was hydrolysed to give the racemic 2-iodomandelic acid (±)-1. Optical resolution of (±)-1 via diastereomeric crystallization with strychnine afforded enantiopure (R)-(−)-1. Absolute configuration of (−)-1 and of its methyl ester (−)-6 was determined by VCD spectroscopy.
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Acknowledgements
The authors thank Professor József Rábai the stimulating discussions and the National Research Development and Innovation Office (K115764), and the Central Hungarian Operational Program (KMOP-4.2.1/B-10-2011-0002) for supporting this work.
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Nemes, A., Vass, E., Jalsovszky, I. et al. Synthesis of enantiopure 2-iodomandelic acid and determination of its absolute configuration by VCD spectroscopy. Chem. Pap. 73, 47–54 (2019). https://doi.org/10.1007/s11696-018-0568-6
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DOI: https://doi.org/10.1007/s11696-018-0568-6