Fenvalerate → (alphaS)-4-Chloro-alpha-(1-methylethyl)benzeneacetic acid

HRID 1106222

Reaction equation

HRID 1106222 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]=1

Participants

4

Reactant 1

HCID 3347Fenvalerate2×

Product 1

HCID 854132(alphaS)-4-Chloro-alpha-(1-methylethyl)benzeneacetic acid

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

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.

Sources & evidence

ORD record
ord-89baf99e75394998ae7cfacb63ae062a
Source dataset
uspto-grants-1982_01
Patent number
US04312816

Linked notes

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