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

HRID 649627

반응식

HRID 649627 반응식
[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]

참가 물질

4

반응물 2

HCID 5360545SodiumHCID 11557959HCID 11557959, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aecbc8724d084051801745051ecbcac1
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04740612

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