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

HRID 1290720ノート

反応式

HRID 1290720 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-84cf9f2e53b245d38070162b80170c32
出典データセット
uspto-grants-1998_05
特許番号
US05753641

反応ノート

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