Hydrochloric Acid → 4-Hydroxy-3-[2-(4-methylphenyl)ethyl]benzofuran

HRID 230872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230872
[OH:1][C:2]1[C:7]([C:8](=O)[CH:9]=[CH:10][CH:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH2:12]2)=[C:6]([O:19][CH2:20]C(OC)=O)[CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl>CO>[OH:1][C:2]1[C:7]2[C:8]([CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)=[CH:20][O:19][C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 671360496'-Hydroxy-2'-methoxycarbonylmethoxy-4-methyldihydrochalcone

Produkt 1

HCID 231035724-Hydroxy-3-[2-(4-methylphenyl)ethyl]benzofuranAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 6′-hydroxy-2′-methoxycarbonylmethoxy-4-methyldihydrochalcone (0.58 g) in methanol (10 mL) was added sodium methoxide (28% methanol solution, 0.68 mL), and the mixture was heated for reflux overnight. The reaction mixture was cooled to room temperature and poured into 1 mol/L hydrochloric acid. The resulting mixture was extracted with ethyl acetate, and the extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1) to give the title compound (0.13 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperaturefor reflux overnight
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-45381cca27e14a78ae6f16510cbbc7a6
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566699B2

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