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

HRID 566071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566071
[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

Komponenten

7

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bd422caff72f40f387f2e01f155c6a1c
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172061B2

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