Potassium Hydroxide → Permethric acid

HRID 904749Notes

Reaction equation

HRID 904749 reaction equation
C([O:3][C:4]([CH:6]1[CH:8]([CH:9]=[C:10]([Cl:12])[Cl:11])[C:7]1([CH3:14])[CH3:13])=[O:5])C.[OH-].[K+]>O>[CH3:13][C:7]1([CH3:14])[CH:8]([CH:9]=[C:10]([Cl:12])[Cl:11])[CH:6]1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl ester

Product 1

HCID 91658Permethric acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

24.7 g. of 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropane-1-carboxylic acid ethyl ester (purity: 96%, cis)trans ratio: 40:60), 6.7 g. of a 30% aqueous potassium hydroxide solution and 0.05 g. of polyoxyethylenesorbitane monooleate are stirred at 70° C. for 60 minutes. Stirring is continued with a further 6-g. portion of the potassium hydroxide solution for 60 minutes and with an additional 6-g. portion for 120 minutes. The solution is diluted with 100 ml. of water and 40 ml. fraction is distilled off to remove volatile, non-hydrolyzed substances. To the residual aqueous solution 80 cm3 of hexane is added followed by the addition of 12 g. of a 36% aqueous hydrochloric acid solution at 60° C. with stirring. The reaction mixture is then further manufactured as described in Example 1. 19.8 g. (95%) of 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane-1-carboxylic acid are obtained. Cis/trans ratio: 40:60.

Workup

  1. additionThe solution is diluted with 100 ml
  2. distillationfraction is distilled off
  3. customto remove volatile
  4. additionTo the residual aqueous solution 80 cm3 of hexane is added
  5. additionfollowed by the addition of 12 g
  6. stirringof a 36% aqueous hydrochloric acid solution at 60° C. with stirring

Sources & evidence

ORD record
ord-ff81da0876484cc387ac19efc7a205bc
Source dataset
uspto-grants-1983_12
Patent number
US04419524

Reaction notes

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