Sodium Hydroxide → Permethric acid

HRID 649630Notes

Reaction equation

HRID 649630 reaction equation
[OH-].[Na+].C[C:4]([CH:6]1[CH:8]([CH2:9][C:10](Cl)([Cl:12])[Cl:11])[C:7]1([CH3:15])[CH3:14])=[O:5].BrBr.S([O-])([O-])=[O:19].[Na+].[Na+]>O.CO>[CH3:14][C:7]1([CH3:15])[CH:8]([CH:9]=[C:10]([Cl:12])[Cl:11])[CH:6]1[C:4]([OH:5])=[O:19]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 24437Sodium SulfiteHCID 14181813HCID 14181813, compound

Product 1

HCID 91658Permethric acidYield 72.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To 250 ml of methanol solution containing 24 g of sodium hydroxide were added 17 g of 2,2-dimethyl-3-(2',2',2'-trichloroethyl)-cyclopropyl methyl ketone (purity: 97.9%, cis/trans ratio 91.5/8.5) under cooling with ice, and then 40 g of bromine were added dropwise at -10° C. to -5° C. for 20 minutes and after stirring the mixture at the same temperature for 2 hours, 25.2 g of sodium sulfite (7 hydrate) and 250 ml of water were added thereto, and the mixture was heated up to 70° C. and stirred for 47 hours with heating. Then the methanol was distilled off, water was added to the reaction mixture and neutral part was removed by extraction with ether. The water layer was acidified with conc. hydrochloric acid under cooling with ice. The deposited crystals were filtered, washed with water and dried to obtain 9.85 g of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid, cis/trans ratio 89.8/10.2, purity 91.8%, yield 72.9%.

Workup

  1. temperatureunder cooling with ice
  2. stirringstirred for 47 hours
  3. temperaturewith heating
  4. distillationThen the methanol was distilled off
  5. additionwater was added to the reaction mixture and neutral part
  6. customwas removed by extraction with ether
  7. temperatureunder cooling with ice
  8. filtrationThe deposited crystals were filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-1f3afac383a64e809a90028348200fb2
Source dataset
uspto-grants-1988_04
Patent number
US04740612

Reaction notes

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