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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
  • 31 Downloads

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 

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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