Methyl Ethyl Ketone → 2,3-Dimethyl-4-{[4-(2-methylpropyl)phenyl]methoxy}benzaldehyde

HRID 1003251Notes

Reaction equation

HRID 1003251 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[C:3]=1[CH3:11].[CH2:12]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].CC(CC)=O>C(OCC)(=O)C>[CH2:12]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[C:3]=2[CH3:11])=[CH:22][CH:23]=1)[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 146204471-(Bromomethyl)-4-(2-methylpropyl)benzeneHCID 146949984-Hydroxy-2,3-dimethylbenzaldehyde

Product 1

HCID 146949992,3-Dimethyl-4-{[4-(2-methylpropyl)phenyl]methoxy}benzaldehydeYield 88.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxy-2,3-dimethyl-benzaldehyde (220 mg), 4-isobutylbenzyl bromide (341 mg), potassium carbonate (1.38 g) and ethyl methyl ketone (10 ml) was refluxed for 6 hrs. After cooling, the reaction mixture was diluted with ethyl acetate, the solution was washed with dil hydrochloric acid, water, successively, dried and evaporated. The residue was purified by column chromatography on silica gel (hexane:EtOAc=10:1) to give the title compound (383 mg) having the following physical data:

Workup

  1. temperaturewas refluxed for 6 hrs
  2. temperatureAfter cooling
  3. washthe solution was washed with dil hydrochloric acid, water
  4. customsuccessively, dried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (hexane:EtOAc=10:1)

Sources & evidence

ORD record
ord-efa22c15e5a34681826d50c739c3aa28
Source dataset
uspto-grants-2000_04
Patent number
US06046183

Reaction notes

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