Hydrochloric Acid → Diethyl 2-(4-methoxyphenyl)malonate

HRID 1738672

Reaktionsgleichung

Reaktionsgleichung von HRID 1738672
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.[C:15](=O)([O:19]CC)[O:16][CH2:17][CH3:18].[H-].[Na+].Cl>CN(C)C=O>[CH2:13]([O:12][C:10]([CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:15]([O:16][CH2:17][CH3:18])=[O:19])=[O:11])[CH3:14]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 84174Ethyl 4-methoxyphenylacetate

Produkt 1

HCID 2785178Diethyl 2-(4-methoxyphenyl)malonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

27.7 g of ethyl 4-methoxyphenylacetate and 34 ml of diethyl carbonate were dissolved in 150 ml of N,N-dimethylformamide, and the solution was subjected to reflux under heating, while gradually adding 6.5 g of sodium hydride for 1 hour. After further refluxing under heating for 2 hours, the resulting reaction solution was poured into a mixture of ice water and hydrochloric acid, followed by extraction with ethyl acetate. The resulting organic layer was washed with water, and then dried to distill off the solvent. The residue thus obtained was purified by silica gel column chromatography using toluene as an eluant, thereby obtaining 26.7 g of ethyl 2-ethoxycarbonyl-2-(4-methoxyphenyl)acetate in the form of light yellow oil.

Aufarbeitung

  1. temperatureto reflux
  2. temperatureunder heating
  3. temperatureAfter further refluxing
  4. temperatureunder heating for 2 hours
  5. customthe resulting reaction solution
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe resulting organic layer was washed with water
  8. customdried
  9. distillationto distill off the solvent
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cb7c7149100642379d1d2ffb3672023e
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962695

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