Hydrochloric Acid → 4,6-Di-tert-butyl-5-hydroxybenzofuran

HRID 1376999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376999
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:12]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:13][C:14]2[O:18][C:17](CCCCCCCC)=[CH:16][C:15]=2[C:27]=1[C:28]([CH3:31])([CH3:30])[CH3:29])(=O)C.O.Cl>O1CCCC1>[C:28]([C:27]1[C:15]2[CH:16]=[CH:17][O:18][C:14]=2[CH:13]=[C:12]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:11]=1[OH:10])([CH3:31])([CH3:30])[CH3:29]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 184331765-Acetoxy-4,6-di-tert-butyl-2-octylbenzofuranHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 117707334,6-Di-tert-butyl-5-hydroxybenzofuranAusbeute 132,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium aluminum hydride (0.26 g) was suspended in tetrahydrofuran (50 ml) under a nitrogen atmosphere and a solution of 5-acetoxy-4,6-di-tert-butyl-2-octylbenzofuran (2.7 g) in tetrahydrofuran (20 ml) was added to the suspension under cooling with ice. After heating under reflux for 3 h, the mixture was cooled to room temperature and water was added dropwise. After adding 10% aqueous HCl (50 ml), the mixture was subjected to extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4,6-di-tert-butyl-5-hydroxybenzofuran [2.2 g (yield, 92%)] as a colorless oil.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. temperatureAfter heating
  3. temperatureunder reflux for 3 h
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b43bfe3b73a8430baf06842987c352fd
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663373

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