Hydrochloric Acid → 3-Nitrostilbene

HRID 2230950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2230950
[H-].[Na+].[CH2:3](P(=O)(OCC)OCC)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O)([O-:20])=[O:19].Cl>CN(C)C=O>[N+:18]([C:21]1[CH:22]=[C:23](/[CH:24]=[CH:3]/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:26]=[CH:27][CH:28]=1)([O-:20])=[O:19]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 74493-NitrobenzaldehydeHCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydride

Produkt 1

HCID 9775603-NitrostilbeneAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (60% in oil, 1.48 g) in N,N-dimethylformamide (40 ml) was added a solution of diethyl benzylphosphonate (7.69 g) in N,N-dimethylformamide (40 ml) at 0° C. The mixture was stirred at room temperature for 30 minutes, then a solution of 3-nitrobenzaldehyde (5.09 g) was added thereto. After stirring at 50° C. for 1 hour, the mixture was poured into dilute hydrochloric acid, and extracted with ethyl acetate 3 times. The combined organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give (E)-3-nitrostilbene (3.97 g).

Aufarbeitung

  1. stirringAfter stirring at 50° C. for 1 hour
  2. extractionextracted with ethyl acetate 3 times
  3. washThe combined organic solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant solid was collected
  7. washwashed with isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7019ddeae2b44f5daee461f10470ce30
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06426345B1

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