Methyltriphenylphosphonium iodide → 3,5-Bis(3',5'-di-t-butylstyryl)styrene

HRID 2085891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085891
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[C:28]([C:32]1[CH:33]=[C:34]([CH:61]=[C:62]([C:64]([CH3:67])([CH3:66])[CH3:65])[CH:63]=1)[CH:35]=[CH:36][C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([CH:45]=[CH:46][C:47]2[CH:52]=[C:51]([C:53]([CH3:56])([CH3:55])[CH3:54])[CH:50]=[C:49]([C:57]([CH3:60])([CH3:59])[CH3:58])[CH:48]=2)[CH:44]=1)[CH:40]=O)([CH3:31])([CH3:30])[CH3:29]>O1CCCC1>[C:28]([C:32]1[CH:33]=[C:34]([CH:61]=[C:62]([C:64]([CH3:67])([CH3:66])[CH3:65])[CH:63]=1)[CH:35]=[CH:36][C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([CH:45]=[CH:46][C:47]2[CH:52]=[C:51]([C:53]([CH3:56])([CH3:55])[CH3:54])[CH:50]=[C:49]([C:57]([CH3:60])([CH3:59])[CH3:58])[CH:48]=2)[CH:44]=1)[CH:40]=[CH2:2])([CH3:31])([CH3:30])[CH3:29]

Komponenten

5

Edukt 3

HCID 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxideHCID 540286873,5-Bis[2-(3,5-di-tert-butylphenyl)ethenyl]benzaldehyde

Produkt 1

HCID 538517063,5-Bis(3',5'-di-t-butylstyryl)styreneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dry tetrahydrofuran (375 mL) was added to a mixture of methyltriphenylphosphonium iodide (50.6 g, 125 mmoles) and potassium t-butoxide (14.0 g, 125 mmoles) and stirred at room temperature for 15 minutes. 3,5-bis(3′,5′-di-t-butylstyryl)benzaldehyde (44.6 g, 83.4 mmoles) was then added and the reaction mixture was stirred at room temperature for 90 minutes. The solvent was then evaporated and the remaining sludge was triturated with dichloromethane—pet.ether (40-60) (1:9) and filtered through silica, rinsing thoroughly with the same solvent mixture. The crude product was recrystallised from dichloromethane/methanol to give white crystals of 3,5-bis(3′,5′-di-t-butylstyryl)styrene (42.15 g, 95%) m.p. 143-145° C. with microanalysis i/r, u/v, NMR and mass spectrographic data substantially identical to that of the first example.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 90 minutes
  2. customThe solvent was then evaporated
  3. customthe remaining sludge was triturated with dichloromethane—pet
  4. filtrationether (40-60) (1:9) and filtered through silica
  5. washrinsing thoroughly with the same solvent mixture
  6. customThe crude product was recrystallised from dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-a9d85e97c851424d873731c8df8200f0
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720093B2

Notizen zur Reaktion

Wird geladen…