Methanol → Permethric acid

HRID 649628Notes

Reaction equation

HRID 649628 reaction equation
CO.[OH-].[Na+].[CH3:5][C:6]1([CH3:17])[CH:8]([CH2:9][C:10](Cl)([Cl:12])[Cl:11])[CH:7]1[C:14]([OH:16])=[O:15]>O>[CH3:5][C:6]1([CH3:17])[CH:8]([CH:9]=[C:10]([Cl:12])[Cl:11])[CH:7]1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12546554HCID 12546554, compound

Product 1

HCID 91658Permethric acidYield 86.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 120 ml of methanol solution containing 4.8 g of sodium hydroxide were added 11.1 g of 2,2-dimethyl-3-(2',2',2'-trichloroethyl)-cyclopropanecarboxylic acid (purity: 91.8%, cis/trans ratio: 82.8/17.2) to heat the resulting mixture for 37 hours under reflux. The mixture was diluted with water and neutral part was removed by extraction with ether. The water layer was acidified with conc. hydrochloric acid and extracted with ether. The ether layer was concentrated to obtain 8.15 g of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid, cis/trans ratio 79.8/20.2, purity 92.4%, yield 86.8%.

Workup

  1. temperatureto heat the resulting mixture for 37 hours
  2. temperatureunder reflux
  3. customwas removed by extraction with ether
  4. extractionextracted with ether
  5. concentrationThe ether layer was concentrated

Sources & evidence

ORD record
ord-24a68bad848140d98ef0d28deddc7fd9
Source dataset
uspto-grants-1988_04
Patent number
US04740612

Reaction notes

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