Chemical Properties
White to pale cream crystalline powder
Uses
2-Chloromandelic acid, is used as a pharmaceutical intermediate as well as in the medicine industry. It is used as a intermediate of clopidrogrel.
General Description
2-Chloromandelic acid (2-ClMA) is a mandelic acid derivative. A report based on its solid state-NMR, X-ray powder diffraction (XPRD) and Fourier transform infrared spectroscopy (FTIR) data reveals that in solid state 2-ClMA exists as a racemic compound. The study also suggests that the crystals of racemic 2-ClMA belongs the monoclinic space group
P21/
c. The efficiency of (
R)-(+)-
N-benzyl-1-phenylethylamine in resolving racemate 2-ClMA has been investigated.
Synthesis
First, 150 mL of toluene was added to a flask equipped with a stirrer and an internal thermometer. Under stirring conditions, 0.09 g (0.08 x 10^-3 mol) of the (R,R)-VO salen complex from Example 1 and 21.1 g (0.15 mol) of freshly prepared 2-chlorobenzaldehyde were added sequentially. Subsequently, 10.1 g (0.375 mol) of hydrocyanic acid was added all at once. The resulting dark green homogeneous solution was stirred for 24 h at room temperature in a closed apparatus. The conversion was analyzed by gas chromatography (GC) to be 98% and the enantiomeric excess (ee) value of (S)-2-chloromandelate cyanohydrin was 73%.
References
[1] Patent: US2004/236129, 2004, A1. Location in patent: Page 4
