Methanol → Permethric acid

HRID 649629Notes

Reaction equation

HRID 649629 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:4]([CH2:5][C:6](Cl)([Cl:8])[Cl:7])[CH:3]1[C:10]([O:12]C)=[O:11].[OH-].[Na+].CO>O>[CH3:1][C:2]1([CH3:14])[CH:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[CH:3]1[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11557959Methyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropane-1-carboxylate

Product 1

HCID 91658Permethric acidYield 81.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In similar way to that in Stage IV-1 Example 3 above except that 5 g of methyl 2,2-dimethyl-3-(2',2',2'-trichloroethyl)-cyclopropanecarboxylate (purity: 95.8%, cis/trans: 92.7/7.3) were added to a mixture of 4 g of sodium hydroxide, 20 ml of methanol and 30 ml of water to heat the resulting mixture for 10 hours under reflux, 3.31 of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid, cis/trans ratio 98.8/1.2, purity 96.4%, yield 81.7% were obtained.

Workup

  1. temperatureto heat the resulting mixture for 10 hours
  2. temperatureunder reflux

Sources & evidence

ORD record
ord-54a1577f1a344eb19b772a7f2b72315e
Source dataset
uspto-grants-1988_04
Patent number
US04740612

Reaction notes

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