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Chemical Papers

, Volume 73, Issue 1, pp 47–54 | Cite as

Synthesis of enantiopure 2-iodomandelic acid and determination of its absolute configuration by VCD spectroscopy

  • Anikó NemesEmail author
  • Elemér Vass
  • István Jalsovszky
  • Dénes SzabóEmail author
Original Paper
First Online:
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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.

Keywords

Mandelic acid derivatives Building block Optical resolution Determination of absolute configuration 
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Notes

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.

Supplementary material

11696_2018_568_MOESM1_ESM.docx (1.6 mb)
Supplementary material 1 (DOCX 1681 kb)

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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2018

Authors and Affiliations

  1. 1.Institute of ChemistryEötvös Loránd UniversityBudapestHungary

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