Fenvalerate → (alphaS)-4-Chloro-alpha-(1-methylethyl)benzeneacetic acid
Reaction equation
[CH3:1][CH:2]([CH:4]([C:12]([O:14]C(C1C=CC=C(OC2C=CC=CC=2)C=1)C#N)=[O:13])[C:5]1[CH:6]=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=1)[CH3:3]>C(O)C.[Pt]=O>[Cl:11][C:8]1[CH:7]=[CH:6][C:5]([C@H:4]([CH:2]([CH3:3])[CH3:1])[C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The optical purity of the acid moiety of fenvalerate A was determined as follows: Fenvalerate A was hydrogenated in ethanol using platinum oxide as a catalyst to obtain (S)-2-(4-chlorophenyl)isovaleric acid which was then converted to an acid chloride using thionyl chloride. The acid chloride was converted to the l-menthol ester with l-menthol. The ratio between the two resulting diastereomers was determined by gas chromatography, and the optical purity of the acid moiety was calculated.