(S)-(+)-Mandelic acid

Chemical properties

white to light yellow crystal powde

The Uses of (S)-(+)-Mandelic acid

(S)-(+)-Mandelic acid is a versatile reagent used in the resolution of racemates and the preparation of amides, Pharmaceutical Intermediates.

The Uses of (S)-(+)-Mandelic acid

Antiseptic (urinary).

The Uses of (S)-(+)-Mandelic acid

A versatile reagent used in the resolution of racemates and the preparation of amides.

Definition

ChEBI: (S)-mandelic acid is a (2S)-2-hydroxy monocarboxylic acid and a mandelic acid. It is a conjugate acid of a (S)-mandelate. It is an enantiomer of a (R)-mandelic acid.

Flammability and Explosibility

Not classified

Description

(S)-Mandelic acid was converted into chiral pseudo-18-crown-6 ether containing a carboxylic acid group at the 4-position of 2,6-disubstituted methoxyphenyl group through many steps. It was found to afford both a resolution via crystallization as well as epimerization of the chiral center, setting the stage for a DKR.

Purification Methods

Purify the mandelic acids by recrystallisation from H2O, *C6H6 or CHCl3. [Roger J Chem Soc 2168 1932,Jamison & Turner J Chem Soc 611 1942.] They have solubilities in H2O of ca 11% at 25o. [Banks & Davies J Chem Soc 73 1938.] The S-benzylisothiuronium salts has m 180o (from H2O) and [] D 25 (+) and (-) 57o (c20, EtOH) [El Masri et al. Biochem J 68 199 1958]. [Beilstein 10 IV 564.]