Hydrochloric Acid → Z-(1R,S)-cis-2,2-dimethyl-3-(2,2-chloro-3,3,3-trifluoro-1-propenyl)cyclopropanecarboxylic acid

HRID 2165355Notes

Reaction equation

HRID 2165355 reaction equation
Cl.[Cl:2]/[C:3](/[C:13]([F:16])([F:15])[F:14])=[CH:4]\[C@@H:5]1[C@H:7]([C:8]([OH:10])=[O:9])[C:6]1([CH3:12])[CH3:11].Cl/C(/C(F)(F)F)=C\[C@H]1[C@H](C(O)=O)C1(C)C>C(Cl)Cl>[Cl:2][C:3]([C:13]([F:14])([F:15])[F:16])=[CH:4][CH:5]1[CH:7]([C:8]([OH:10])=[O:9])[C:6]1([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11184106(1S-cis)-Cyhalothric acidHCID 12942379trans-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 156507Z-(1R,S)-cis-2,2-dimethyl-3-(2,2-chloro-3,3,3-trifluoro-1-propenyl)cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The aqueous alkali phase was acidified with hydrochloric acid, and the precipitated product was isolated by extraction with methylene chloride, giving 341 g of a crystalline mass comprising 92 g of cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid and 206 g of trans-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid.

Workup

  1. customgiving 341 g of a crystalline mass

Sources & evidence

ORD record
ord-753bbbd25d5040f9b7471208a5aa1713
Source dataset
uspto-grants-1990_07
Patent number
US04939303

Reaction notes

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