Potassium Hydroxide → Permethric acid

HRID 746294Notes

Reaction equation

HRID 746294 reaction equation
[CH3:1][C:2]1([CH3:15])[CH:4]([CH2:5][C:6](Cl)([Cl:8])[Cl:7])[CH:3]1[C:10]([O:12]CC)=[O:11].[OH-].[K+]>>[CH3:1][C:2]1([CH3:15])[CH:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[CH:3]1[C:10]([OH:12])=[O:11]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 108413Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2,2,2-trichloroethyl)-, ethyl ester

Product 1

HCID 91658Permethric acid

Procedure

Ethyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate was hydrolyzed with caustic potash to give 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylic acid, and was converted into the diastereomeric (+)-octyl ester, which was analyzed by gas chromatography. The results were: (+)-cis, 83.6%; (-)-cis, 3.9%; (+)-trans, 7.5%; (-)-trans, 5.0%. The e.e. was calculated to be 91% for the cis isomer and 20% for the trans isomer.

Sources & evidence

ORD record
ord-d3946b3899ad4e69939855f6de4a06e1
Source dataset
uspto-grants-1986_07
Patent number
US04603218

Reaction notes

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