Chemical Properties
clear colorless to light yellow liquid
Uses
Used in the synthesis of natural products and pheromones.
Uses
(S)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride is used in the preparation of natural products and pheromones. It is also employed as a derivatization enantiomeric purity reagent used for the determination of enantiomeric purity of alcohol and amines by gas chromatography.
Uses
Resolution of enantiomers primarily of alcohols and amines.
General Description
(
S)-(+)-α-Methoxy-α-trifluoromethylphenylacetyl chloride is commonly used as a derivatizing agent in Mosher ester analysis and Mosher amide analysis, which are NMR-based methods for determining the absolute configuration of the chiral carbon center in secondary alcohols and amines, respectively.
Purification Methods
The most likely impurity is the free acid due to hydrolysis and should be checked by IR. If free from acid, then distil, taking care to keep moisture out of the apparatus. Otherwise add SOCl2 and reflux for 5hours and distil it. Note that shorter reflux times result in a higher boiling fraction (b 130-155o/1mm) which has been identified as the anhydride. [Dale et al. J Org Chem 34 2543 1969, for enantiomeric purity see Dale & Mosher J Am Chem Soc 97 512 1973.]
