Diethyl Oxalate → Ethyl 4-(3-ethoxy-2,3-dioxopropyl)-3-nitrobenzoate

HRID 1748241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748241
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH2:16]([O:18][C:19](=[O:25])[C:20](OCC)=[O:21])[CH3:17].[O-]CC.[Na+]>C(O)C>[CH2:16]([O:18][C:19](=[O:25])[C:20](=[O:21])[CH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14])[CH3:17]

Komponenten

5

Edukt 3

HCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 14945864Ethyl 4-methyl-3-nitrobenzoate

Produkt 1

HCID 58767563Ethyl 4-(3-ethoxy-2,3-dioxopropyl)-3-nitrobenzoateAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-methyl-3-nitrobenzoate (80 g, 0.38 mol) and oxalic acid diethyl ester (57 mL, 0.42 mol) in ethanol (1000 mL) is added sodium ethoxide (430 mL, 1.15 mol, 21% in ethanol). The resulting brown solution is stirred at room temperature for 16 h. The reaction is quenched with 3N HCl to neutral pH and diluted with water (2000 mL). The resulting white precipitate is filtered and dried in vacuum to afford the title compound (91 g, 77%).

Aufarbeitung

  1. customThe reaction is quenched with 3N HCl to neutral pH
  2. additiondiluted with water (2000 mL)
  3. filtrationThe resulting white precipitate is filtered
  4. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-06eaffc7111d475cbd130299e6ebe52c
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150577B2

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