Hydrochloric Acid → Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, methyl ester

HRID 1763975Notes

Reaction equation

HRID 1763975 reaction equation
[Na].Cl.[CH3:3][C:4]([CH3:17])([CH:11](Cl)[CH:12]=[C:13]([Cl:15])[Cl:14])[CH2:5][C:6]([O:8][CH2:9]C)=[O:7]>CO>[CH3:3][C:4]1([CH3:17])[CH:11]([CH:12]=[C:13]([Cl:15])[Cl:14])[CH:5]1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3042523Ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoateHCID 5360545Sodium

Product 1

HCID 94591Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.4 Part of metallic sodium was dissolved in 30 parts of anhydrous methanol, and 2.7 parts of ethyl 3,3-dimethyl-4,6,6-trichloro-5-hexenoate prepared in the same manner as in Example 3 was added to the solution. The mixture was agitated for 2 hours under reflux of methanol. The liquid reaction mixture was cooled with ice water and neutralized with hydrogen chloride-saturated methanol. The precipitated solids were removed by filtration, and the filtrate was concentrated until the volume was reduced to 1/10. The concentrate was diluted with diethyl ether, washed with water and dried. Then, the solvent was removed by distillation, and the residue was subjected to distillation under reduced pressure to obtain 2.0 parts of methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropane-carboxylate having a boiling point of 68° - 70° C. under 0.2 mm Hg. The yield was 90 %. the cis : trans ratio of the product determined by gas chromatography was 22 : 78.

Workup

  1. customprepared in the same manner as in Example 3
  2. additionwas added to the solution
  3. customThe liquid reaction mixture
  4. customThe precipitated solids were removed by filtration
  5. concentrationthe filtrate was concentrated until the volume
  6. additionThe concentrate was diluted with diethyl ether
  7. washwashed with water
  8. customdried
  9. customThen, the solvent was removed by distillation
  10. distillationthe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-6dbc065c105b49f98c9acc3d071f6914
Source dataset
uspto-grants-1978_09
Patent number
US04113968

Reaction notes

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