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

HRID 411932Notes

Reaction equation

HRID 411932 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4860cb35bd794a1491f259d2134c0638
Source dataset
uspto-grants-2003_05
Patent number
US06558818B1

Reaction notes

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