Nitric Acid → 4-(2-Chloroethoxy)-5-methoxy-2-nitrobenzaldehyde

HRID 989390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989390
[N+:1]([O-:4])(O)=[O:2].[Cl:5][CH2:6][CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH3:18]>ClCCCl>[Cl:5][CH2:6][CH2:7][O:8][C:9]1[C:10]([O:17][CH3:18])=[CH:11][C:12]([CH:13]=[O:14])=[C:15]([N+:1]([O-:4])=[O:2])[CH:16]=1

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 107750234-(2-Chloroethoxy)-3-methoxybenzaldehyde

Produkt 1

HCID 219563824-(2-Chloroethoxy)-5-methoxy-2-nitrobenzaldehydeAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Fuming nitric acid (10 mL) is added dropwise to a −40° C. suspension of 5.00 g (23.36 mmol) of 4-(2-chloroethoxy)-3-methoxybenzaldehyde (Milbank, J. B. J., et. al., J. Med. Chem., 42(4), 649-658, 1999) in 23 mL of 1,2-dichloroethane. The reaction mixture is slowly allowed to warm to −10° C. The mixture is poured onto 300 mL of ice water and then extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. Diethyl ether is added to the residue and the pale yellow solid is collected by filtration to provide 2.43 g (40%) of 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzaldehyde, mp 148-150° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionDiethyl ether is added to the residue
  6. filtrationthe pale yellow solid is collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-072dc079392344c8bbaff9ac7698360b
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638929B2

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