ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Anikó Nemes, Elemér Vass, István Jalsovszky, and Dénes Szabó

Eötvös Loránd University, Budapest, Hungary

E-mail: neagaft@elte.hu

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 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-018-0568-6

Chemical Papers 73 (1) 47–54 (2019)