Hydrochloric Acid → Permethric acid

HRID 904747Notes

Reaction equation

HRID 904747 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-].[Na+].C(OS(C1C=CC=CC=1)(=O)=O)CCCCCCCCCCC.[Na].Cl>CCCCCC.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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide3×HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl esterHCID 57371080Sodium dodecylbenzene sulphonate

Product 1

HCID 91658Permethric acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent2×

Procedure

27.9 g. of 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane-1-carboxylic acid ethyl ester (purity: 85%, cis) trans ratio: 40:60/, 6 g. of a 25% aqueous sodium hydroxide solution and 0.01 g. of sodium dodecylbenzene sulfonate are stirred at a temperature of 80° C. for 30 minutes. Hydrolysis is then continued with a further 5 g. portion of sodium hydroxide solution for 60 minutes and subsequently with an additional 5 g. portion of a sodium hydroxide solution for 150 minutes. The mixture is diluted with 30 ml. of water, cooled to 20° C. and the unreacted compounds are dissolved in 10 ml. of hexane. To the aqueous phase 80 ml. of hexane are added and the organic acid is set free by adding 12 g. of a 36% aqueous hydrochloric acid solution with stirring. The hexane solution is separated, decolored with 0.5 g. of activated carbon, filtered, 35 ml. of the solvent are distilled off and the residue is crystallized at -5° C. for 48 hours. The crystals are filtered off and dried. 17.8 g. (85%) of 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropane-1-carboxylic acid are obtained. Cis/trans ratio: 40:60.

Workup

  1. customHydrolysis
  2. additionThe mixture is diluted with 30 ml
  3. dissolutionthe unreacted compounds are dissolved in 10 ml
  4. additionby adding 12 g
  5. customThe hexane solution is separated
  6. filtrationof activated carbon, filtered
  7. distillationof the solvent are distilled off
  8. customthe residue is crystallized at -5° C. for 48 hours
  9. filtrationThe crystals are filtered off
  10. customdried

Sources & evidence

ORD record
ord-086dc95a8ace45d49905e55fd882d7b4
Source dataset
uspto-grants-1983_12
Patent number
US04419524

Reaction notes

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