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

HRID 1290720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1290720
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 146949992,3-Dimethyl-4-{[4-(2-methylpropyl)phenyl]methoxy}benzaldehydeAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxy-2,3-dimethylbenzaldehyde (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:

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-84cf9f2e53b245d38070162b80170c32
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753641

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