Anisole → Ethyl 2-(4-methoxyphenyl)-2-oxoacetate

HRID 1070030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070030
[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:13]1([O:19][CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH3:20][O:19][C:13]1[CH:18]=[CH:17][C:16]([C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 7519AnisoleHCID 20884Ethoxalyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 2758864Ethyl 2-(4-methoxyphenyl)-2-oxoacetateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of aluminum chloride (59.0 g) and dichloromethane (500 ml), ethyl chloroglyoxylate (45.4 ml) was added dropwise at 0° C. After stirring for 15 minutes, anisole (40.1 ml) was added dropwise at 0° C., and the mixture was stirred for 1.5 hours at room temperature. The reaction mixture was poured onto ice (500 g), and the mixture was stirred for 1 hour at room temperature The dichloromethane layer separated was washed with saturated aqueous sodium chloride, dried (MgSO4), and then concentrated. The residue was subjected to column chromatography on silica gel, and ethyl 4-methoxyphenylglyoxylate (43.6 g, yield 60%) was obtained as an oil from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Aufarbeitung

  1. additionwas added dropwise at 0° C
  2. stirringthe mixture was stirred for 1.5 hours at room temperature
  3. additionThe reaction mixture was poured onto ice (500 g)
  4. customseparated
  5. washwas washed with saturated aqueous sodium chloride
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0593cc8e0be94d0eb75f32e66bec3262
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251926B1

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