3-Nitrobenzaldehyde → Methyl 4-[2-(3-nitrophenyl)vinyl]benzoate

HRID 1160384

Reaktionsgleichung

Reaktionsgleichung von HRID 1160384
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)=[O:5].[N+:32]([C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH:38]=O)([O-:34])=[O:33].C1CC23[N+](=[N-])C(CCC2)=C3C1>C(#N)C>[N+:32]([C:35]1[CH:36]=[C:37]([CH:38]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:31][CH:30]=2)[CH:40]=[CH:41][CH:42]=1)([O-:34])=[O:33]

Komponenten

5

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 219219891,5-Diazobicyclo(4.3.0)non-5-ene

Produkt 1

HCID 68690726Methyl 4-[2-(3-nitrophenyl)vinyl]benzoateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

71.2 g of 4-methoxycarbonylbenzyltriphenylphosphonium bromide and 23 g (0.15 M) of 3-nitrobenzaldehyde are added to 360 ml of acetonitrile in a 1000 ml reactor. 19 ml (0.15 M) of 1,5-diazobicyclo[4.3.0]non-5-ene (DBN) are then added and the reaction medium is then refluxed with stirring for 1 hour. The solvent is then evaporated off and the residue obtained is then purified by chromatography on silica, using dichloromethane as eluent. After evaporation, 41.6 g of a white solid are obtained (yield: 95%).

Aufarbeitung

  1. temperaturethe reaction medium is then refluxed
  2. customThe solvent is then evaporated off
  3. customthe residue obtained
  4. customis then purified by chromatography on silica
  5. customAfter evaporation, 41.6 g of a white solid
  6. customare obtained (yield: 95%)

Quellen und Nachweise

ORD-Eintrag
ord-db25ae22fe1a45c58be3ca0a56c10117
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816397B2

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