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4-Nitrobenzaldehyde → 1,2-Bis(4-nitrophenyl)ethanone

HRID 2372369
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2372369
[OH-].[K+].N([CH:10]([C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)P(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[N+:36]([C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[O:44])=[CH:41][CH:40]=1)([O-:38])=[O:37]>CO.C1COCC1>[N+:36]([C:39]1[CH:40]=[CH:41][C:42]([C:43](=[O:44])[CH2:10][C:27]2[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=2)=[CH:45][CH:46]=1)([O-:38])=[O:37]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 5414-NitrobenzaldehydeHCID 14797Potassium HydroxideHCID 12240723HCID 12240723, Verbindung

Produkt 1

HCID 122407241,2-Bis(4-nitrophenyl)ethanoneAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

A solution of KOH (7.56 g, 0.13 mol) in MeOH (75 ml) was added to the phosphonate ester 33 (62.1 g, 0.13 mol) in THF (400 ml) at -78° C. for 0.5 hour and p-nitrobenzaldehyde (20.3 g, 0.13 mol) in 200 ml of THF was added over 0.5 hour. The reaction was warmed to room temperature and stirred an additional 2 hours. THF was removed under reduced pressure. The residue was taken up in EtOAc and washed twice with 5% aqueous NaHCO3 and once with brine. The ethyl acetate was removed under reduced pressure. The dark red enemine was dissolved in CH3OH (600 ml) and concentrated HCl (0.2 ml) was added. The solution was stirred for 1 hour at room temperature and diluted with H2O (500 ml). The solid was filtered, washed with ether and dried to afford 34 (35.6 g, 82.0%), m.p. 131°-133° C.

Aufarbeitung

  1. customTHF was removed under reduced pressure
  2. washwashed twice with 5% aqueous NaHCO3 and once with brine
  3. customThe ethyl acetate was removed under reduced pressure
  4. dissolutionThe dark red enemine was dissolved in CH3OH (600 ml)
  5. additionconcentrated HCl (0.2 ml) was added
  6. stirringThe solution was stirred for 1 hour at room temperature
  7. additiondiluted with H2O (500 ml)
  8. filtrationThe solid was filtered
  9. washwashed with ether
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ef995545ee344040b997866794cd2f2f
Quelldatensatz
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05098918

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