Hydrochloric Acid → 2-(4-Methylphenyl)benzofuran-5-carboxylic acid

HRID 1388001ノート

反応式

HRID 1388001 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.CC1CCCCC=1.Cl([O-])=[O:27].[Na+].P([O-])(O)(O)=O.[Na+].Cl>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]([OH:27])=[O:18])=[CH:13][C:11]=3[CH:12]=2)=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 115741-MethylcyclohexeneHCID 184722462-(4-Methylphenyl)benzofuran-5-carbaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

生成物 1

HCID 184722092-(4-Methylphenyl)benzofuran-5-carboxylic acid収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-(4-methylphenyl)benzofuran-5-carbaldehyde (500 mg) and 1-methylcyclohexene (1.2 ml) in DMF (15 ml) was added a solution (9 ml) of sodium chlorite (80%, 1.5 g) and sodium dihydrogenphosphate (1.5 g) at room temperature, and the mixture was stirred for 3 hours. To the mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with sodium thiosulfate and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the precipitated crystals were collected by filtration, which were washed with diethylether to give colorless crystals of 2-(4-methylphenyl)benzofuran-5-carboxylic acid (395 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with sodium thiosulfate and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationUnder reduced pressure, the mixture was concentrated
  5. filtrationthe precipitated crystals were collected by filtration, which
  6. washwere washed with diethylether

出典と根拠

ORDレコード
ord-31ddca37e8e84b14ae9ef0ba322911fe
出典データセット
uspto-grants-2001_07
特許番号
US06268354B1

反応ノート

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