Water → Permethric acid

HRID 1763974Notes

Reaction equation

HRID 1763974 reaction equation
[Na].O.[CH3:3][C:4]([CH3:17])([CH:11](Cl)[CH:12]=[C:13]([Cl:15])[Cl:14])[CH2:5][C:6]([O:8]CC)=[O:7]>CO>[CH3:17][C:4]1([CH3:3])[CH:11]([CH:12]=[C:13]([Cl:14])[Cl:15])[CH:5]1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 3042523Ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoateHCID 5360545Sodium

Product 1

HCID 91658Permethric acidYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.4 Parts of metallic sodium was dissolved in 50 parts of anhydrous methanol, and 5.5 parts of ethyl 3,3-dimethyl-4,6,6-trichloro-5-hexenoate prepared in the same manner as in Example 1 was added to the solution. The mixture was agitated for 2 hours under reflux of methanol. The liquid reaction mixture was naturally cooled, and 20 parts of water was added thereto and the mixture was agitated at 40° to 50° C. for 2 hours. Then, methanol was distilled under reduced pressure, and the residue was neutralized with hydrochloric acid and extracted with diethyl ether. The ether extract was dried and the ether was distilled to obtain 3.7 parts of the crystal of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropane-carboxylic acid. The yield was 88 % based on ethyl 3,3-dimethyl-4,6,6-trichlorohexenoate.

Workup

  1. customprepared in the same manner as in Example 1
  2. additionwas added to the solution
  3. customThe liquid reaction mixture
  4. temperaturewas naturally cooled
  5. stirringthe mixture was agitated at 40° to 50° C. for 2 hours
  6. distillationThen, methanol was distilled under reduced pressure
  7. extractionextracted with diethyl ether
  8. extractionThe ether extract
  9. customwas dried
  10. distillationthe ether was distilled

Sources & evidence

ORD record
ord-c6a82b6753d1484d842120092823adcb
Source dataset
uspto-grants-1978_09
Patent number
US04113968

Reaction notes

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