Water → 2-(3-Nitrobenzylidene)-3,4-dihydronaphthalen-1(2h)-one

HRID 54586

Reaktionsgleichung

Reaktionsgleichung von HRID 54586
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[C:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]1=[O:11])([O-:14])=[O:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 107241-TetraloneHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 2888042-(3-Nitrobenzylidene)-3,4-dihydronaphthalen-1(2h)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 3,4-dihydro-1(2H)-naphthalenone (21.9 g), 3-nitrobenzaldehyde (22.6 g) and p-toluenesulphonic acid monohydrate (50 mg) in toluene (250 ml) was stirred at reflux with separation of water for 4.5 hours. The brown solution was allowed to cool overnight. The resulting yellow-orange deposited solid was filtered off, washed well with toluene and dried in vacuo yielding 2-(3-nitrobenzylidene)-3,4-dihydro-1(2H)-naphthalenone as crisp yellow needles.

Aufarbeitung

  1. temperatureto cool overnight
  2. filtrationwas filtered off
  3. washwashed well with toluene
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-24bd5505bcae4988aed129c6132f0ea9
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622987

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