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

HRID 1290720노트

반응식

HRID 1290720 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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:

후처리

  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)

출처 및 근거

ORD 기록
ord-84cf9f2e53b245d38070162b80170c32
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753641

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