Benzaldehyde → 2-Benzylidene-1,3-indandione

HRID 990897

Reaktionsgleichung

Reaktionsgleichung von HRID 990897
[B]=O.[CH:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]1(=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C:12]1=O>N1CCCCC1.C1C=CC=CC=1>[CH:13](=[C:12]1[C:3](=[O:10])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:11]1=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 240BenzaldehydeHCID 1233581,2-IndandioneHCID 6327189Boron monoxide

Produkt 1

HCID 2378222-Benzylidene-1,3-indandione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

(8) (Chem. Pharm. Bull. 1974, 22(2), 448-451). Boron oxide (720 mg, 10.26 mmol) and benzaldehyde (800 mg, 7.53 mmol) were added to a stirred solution of the indandione (1.00 g, 6.84 mmol) and piperidine (3 drops) in 10.2 ml of benzene. The solution was refluxed with stirring for 30 minutes. After filtration of the solution, the filtrate was concentrated under reduced pressure. The resulting crystalline solid was recrystallized from ethanol to afford 1.00 g (62.4%) of yellowish-green platelets: mp 149.5-150.0° C. (lit. mp 150° C., Okukawa, et al., Chem. Pharm. Bull., 1974, 22(2), 448-451). 1H NMR (250 MHz) δ 8.47-8.45 (m, 2H), 8.06-7.99 (m, 2H), 7.90 (s, 1H), 7.84-7.79 (m, 2H), 7.58-7.50 (m, 3H); 13C NMR (62.7 MHz) 190.5, 189.2, 147.2, 142.7, 140.2, 135.6, 135.4, 134.3, 133.4, 133.2, 129.3, 129.0, 123.5, 123.5 ppm.

Aufarbeitung

  1. temperatureThe solution was refluxed
  2. filtrationAfter filtration of the solution
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting crystalline solid was recrystallized from ethanol
  5. customto afford 1.00 g (62.4%) of yellowish-green platelets

Quellen und Nachweise

ORD-Eintrag
ord-7cb3bddf1d62412c8322c6bc556bc9ef
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462075B1

Verknüpfte Notizen

Wird geladen…