Acetone → 3,5-Di-t-butylstyrene

HRID 411930Notes

Reaction equation

HRID 411930 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]([C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:18]=1)[CH:14]=O)([CH3:10])([CH3:9])[CH3:8].CC(C)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:7]([C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:18]=1)[CH:14]=[CH2:1])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 180AcetoneHCID 12682533,5-Bis(tert-butyl)benzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 109219283,5-Di-t-butylstyreneYield 93.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Dry tetrahydrofuran (80 ml) was added to a mixture of potassium t-butoxide (6.740 g, 60.06 mmoles) and methyltriphenylphosphonium bromide (24.276 g, 60.06 mmoles) and stirred at room temperature for 30 minutes. A solution of 3,5-di-t-butylbenzaldehyde (10.087 g, 46.20 mmoles) in dry tetrahydrofuran (30 ml) was then added and the reaction mixture was stirred at room temperature for 17 hours. Acetone (50 ml) was then added and then all of the solvent was removed under vacuum. Pet. ether (60-80, 150 ml) was then added to the residue and the mixture was stirred vigorously for 30 minutes. The solution was then filtered through silica, rinsing thoroughly with pet. ether (60-80) and the solvent removed under vacuum to give 3,5-di-t-butylstyrene (9.302 g, 93%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 17 hours
  2. customall of the solvent was removed under vacuum
  3. additionPet. ether (60-80, 150 ml) was then added to the residue
  4. stirringthe mixture was stirred vigorously for 30 minutes
  5. filtrationThe solution was then filtered through silica
  6. washrinsing thoroughly with pet. ether (60-80)
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-6545aeb0162145e7942686cd4591c438
Source dataset
uspto-grants-2003_05
Patent number
US06558818B1

Reaction notes

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