1,3-Indandione → 2-(3,4-dichlorobenzylidene)-1H-indene-1,3(2H)-dione

HRID 1243342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243342
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[CH2:2]1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:16]=O>CCO.N1CCCCC1>[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:16]=[C:2]1[C:1](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:10]

Komponenten

5

Edukt 2

HCID 118151,3-IndandioneHCID 227103,4-Dichlorobenzaldehyde

Produkt 1

HCID 75149132-(3,4-dichlorobenzylidene)-1H-indene-1,3(2H)-dioneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of indan-1,3-dione (1a) (960 mg, 6.6 mmol) in EtOH (8.2 mL) was added 3,4-dichlorobenzaldehyde (1b) (1.3 g, 7.2 mmol) followed by piperidine (3 drops). The reaction mixture was heated to reflux for 30 min. After cooling, the reaction was diluted with EtOH (8 mL) and the precipitate was filtered. The resulting solid was triturated twice with EtOH and dried under high vacuum to give 2-(3,4-dichloro-benzylidene)-indane-1,3-dione (1c) (1.7 g, 82% yield).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 min
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered
  5. customThe resulting solid was triturated twice with EtOH
  6. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f265996ff6da46afb83935f681933a1e
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119099B2

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