Diethyl Ether → 4-Pentenal, 4-methyl-5-(4-methylphenyl)-, (4E)-

HRID 2408242Notes

Reaction equation

HRID 2408242 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12]/[C:13](=[CH:18]\[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)/[CH2:14][CH2:15][CH2:16][OH:17].C(OCC)C>ClCCl>[CH3:12]/[C:13](=[CH:18]\[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)/[CH2:14][CH2:15][CH:16]=[O:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 67332502(4E)-4-Methyl-5-(4-methylphenyl)-4-penten-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 714656444-Pentenal, 4-methyl-5-(4-methylphenyl)-, (4E)-Yield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid pyridinium chlorochromate (13.2 g, 0.06 mol) was added in one portion to a pre-cooled (−10° C.) solution of (4E)-4-Methyl-5-(4-methylphenyl)-4-penten-1-ol (9.88 g, 0.052 mol) in dry dichloromethane (250 ml) under nitrogen. After 30 minutes, the reaction was warmed up to room temperature. After 1 hour, diethyl ether (700 ml) was added to the reaction. After stirring for 10 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 10:1) followed by bulb-to-bulb distillation (100° C./0.001 mbar). 3.55 g (yield=36%) of the desired product were obtained.

Workup

  1. waitAfter 1 hour
  2. filtrationthe reaction was filtered through silica gel
  3. washrinsing with diethyl ether
  4. customThe solvent was removed under vacuum
  5. customthe residue was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 10:1)
  6. distillationfollowed by bulb-to-bulb distillation (100° C./0.001 mbar)

Sources & evidence

ORD record
ord-8624fcc6fc074bab8f5a9aabb8512f0d
Source dataset
uspto-grants-2014_08
Patent number
US08815792B2

Reaction notes

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