Water → 2-(1,3-Dimethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acid

HRID 217291

Reaktionsgleichung

Reaktionsgleichung von HRID 217291
Cl[C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C[O-].[Na+].O.[C:18]([O:25][CH3:26])(=[O:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21]>[Cu]Br>[C:4]([C:3]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=1[CH:19]([C:18]([O:25][CH3:26])=[O:24])[C:20]([O:22][CH3:23])=[O:21])([OH:6])=[O:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 74482-Chloro-4-nitrobenzoic acidHCID 7943Dimethyl malonateHCID 10942334Sodium Methoxide

Produkt 1

HCID 105900782-(1,3-Dimethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acidAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24593copper(I) bromideKatalysator

Versuchsvorschrift

2-Chloro-4-nitrobenzoic acid (7.5 g, 37.2 mmol) was dissolved in deaerated dimethyl malonate (90 mL). Copper (I) bromide (0.54 g, 3.7 mmol) and sodium methoxide (4.83 g, 89.4 mmol) were added to the solution. The mixture was stirred at room temperature for 15 minutes, and then stirred at 70 to 75° C. overnight. After the reaction solution was allowed to return to room temperature, water was added thereto and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (7.0 g, 68%).

Aufarbeitung

  1. stirringstirred at 70 to 75° C. overnight
  2. customto return to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a635430815784b989cdc9500b973476c
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193351B2

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