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Ethanol → 2-(2,4-Dichlorophenyl)-butendioic acid diethyl ester

HRID 322841
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 322841
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])=O)[CH3:2].[Na+].[Cl-].[CH2:18]([O:20][CH2:21][CH3:22])[CH3:19].C([OH:25])C>>[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])=[CH:19][C:18]([O:20][CH2:21][CH3:22])=[O:25])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 2736411Ethyl 2,4-dichlorobenzoylformate

Produkt 1

HCID 536848672-(2,4-Dichlorophenyl)-butendioic acid diethyl esterAusbeute 53 %

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

An ethanolic solution of sodium ethylate, obtained from sodium (3.35 g; 0.1457 moles) and dry ethanol (276 ml), kept under stirring in inert atmosphere, was added at 20° C. with a solution of (2,4-dichloro-phenyl)-oxo-acetic acid ethyl ester obtained as described in example 2 (36 g; 0.147 moles), and triethyl phosphonoacetate (34.2 g; 0.152 moles) in dry ethanol (70 ml). The reaction mixture was then brought and kept at reflux for 16-20 hours. After cooling to 25° C., the mixture was poured under stirring into a solution of saturated NaCl (500 ml), ethyl ether was added (150 ml) and the phases were separated. The aqueous phase was extracted again with ethyl ether (150 ml). The joined organic phases were washed with water (100 ml), anhydrified over dry Na2SO4, evaporated to dryness. The thus obtained residue was purified by chromatography (SiO2; hexane/ethyl ether 9/1) to give 24.6 g of (E) 2-(2,4-dichlorophenyl)-butendioic acid diethyl ester (yield 53%) as a colourless oil.

Aufarbeitung

  1. customobtained
  2. temperatureat reflux for 16-20 hours
  3. additionthe mixture was poured
  4. additionwas added (150 ml)
  5. customthe phases were separated
  6. extractionThe aqueous phase was extracted again with ethyl ether (150 ml)
  7. washThe joined organic phases were washed with water (100 ml)
  8. customover dry Na2SO4, evaporated to dryness
  9. customThe thus obtained residue was purified by chromatography (SiO2; hexane/ethyl ether 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-8f3b6d3f1e1f4fa5b4dabd0b8b9cbd33
Quelldatensatz
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06211387B1

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