Diethyl Ether → 4-Methyl-3-phenyl-4-pentenal

HRID 2387595Notes

Reaction equation

HRID 2387595 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][C:13](=[CH2:24])[CH:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][CH2:16][OH:17].C([O-])(=O)C.[Na+].C(OCC)C>ClCCl>[CH3:24][C:13](=[CH2:12])[CH:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][CH:16]=[O:17]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 146915204-Methyl-3-phenyl-4-penten-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 204881864-Methyl-3-phenyl-4-pentenalYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid pyridinium chlorochromate (110.24 g, 0.5 mol) was added portion-wise to a pre-cooled (−10° C.) mixture of 4-methyl-3-phenyl-4-penten-1-ol (70 g, 0.418 mol) and anhydrous sodium acetate (41.5 g, 0.5 mol) in dry dichloromethane (400 ml) under nitrogen. After 30 minutes, the reaction was warmed up to room temperature. After 4 hours, diethyl ether (1 liter) was added to the reaction. After stirring for 30 minutes, the reaction was filtered through silica gel, rinsing with diethyl ether. The solvent was removed under vacuum and the residue was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1 to 5:1) followed by distillation through a 20-cm Widmer column. 24 g (yield=33%) of the desired product were obtained. B.P.=50° C./0.001 mbar.

Workup

  1. temperaturea pre-cooled
  2. waitAfter 4 hours
  3. filtrationthe reaction was filtered through silica gel
  4. washrinsing with diethyl ether
  5. customThe solvent was removed under vacuum
  6. customthe residue was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1 to 5:1)
  7. distillationfollowed by distillation through a 20-cm Widmer column

Sources & evidence

ORD record
ord-4c65d1e0a71642f88a4b191c1afda763
Source dataset
uspto-grants-2012_09
Patent number
US08268895B2

Reaction notes

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