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

HRID 649627

Reaction equation

HRID 649627 reaction equation
[Na].[CH3:2][C:3]1([CH3:15])[CH:5]([CH2:6][C:7](Cl)([Cl:9])[Cl:8])[CH:4]1[C:11]([O:13][CH3:14])=[O:12]>CO>[CH3:2][C:3]1([CH3:15])[CH:5]([CH:6]=[C:7]([Cl:8])[Cl:9])[CH:4]1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 11557959HCID 11557959, compound

Product 1

HCID 94591Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, methyl esterYield 80.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 80 ml of methanol solution containing 0.92 g of metallic sodium were added 7.8 g of methyl 2,2-dimethyl-3-(2',2',2'-trichloroethyl)-cyclopropanecarboxylate (purity: 87.8%, cis/trans ratio: 88/12) to heat the resulting mixture for 35 hours under reflux. After distilling off the methanol, the mixture was diluted with water, acidified with diluted hydrochloric acid, subjected to extraction with ether. After washing the ether layer with sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, the ether was distilled off. Vacuum distillation was carried out to obtain 5.4 g of methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate, b.p. 64°-72° C./1.2 mmHg, cis/trans ratio 90.9/9.1, purity 87.8%, yield 79.8%. Further, the sodium bicarbonate aqueous wash solution was acidified to obtain 0.5 g of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid.

Workup

  1. temperatureto heat the resulting mixture for 35 hours
  2. temperatureunder reflux
  3. distillationAfter distilling off the methanol
  4. additionthe mixture was diluted with water
  5. extractionsubjected to extraction with ether
  6. washAfter washing the ether layer with sodium bicarbonate aqueous solution
  7. distillationa saturated sodium chloride aqueous solution, the ether was distilled off
  8. distillationVacuum distillation

Sources & evidence

ORD record
ord-aecbc8724d084051801745051ecbcac1
Source dataset
uspto-grants-1988_04
Patent number
US04740612

Linked notes

Loading…