Tetrahydrofuran → 4-Hydroxy-4'-(1-hydroxyethyl)biphenyl

HRID 2380166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2380166
C(O[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.[O:18]1CC[CH2:20][CH2:19]1.[BH4-].[Na+]>CO>[OH:18][CH:19]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)[CH3:20]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 144384094-Methylcarbonyloxy-4'-hydroxybiphenyl

Produkt 1

HCID 139308004-Hydroxy-4'-(1-hydroxyethyl)biphenylAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution containing 4-acetoxy-4'-hydroxy-1,1'-biphenyl from part A (5.0 g, 23.6 mmol) in methanol (500 mL) and tetrahydrofuran (30 mL) is treated with sodium borohydride (0.9 g, 23.8 mmol) in portions over 30 minutes at room temperature. After 2 hours, the reaction mixture is concentrated under reduced pressure, diluted with water (400 mL), acidified with 2N HCl and extracted with ethyl acetate. The organic layer is washed with water and brine, dried over MgSO4 and concentrated to a solid residue. Crystallization of the solid from ethyl acetate gives 4.7 g (92.9%) of the title compound, m.p. 159°-160° C.; MS (El m/z): 214 (M)+ and 199 (b.p. M-CH3)+.

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. additiondiluted with water (400 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a solid residue
  7. customCrystallization of the solid from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c862cfaf2d8e4603b188723b52d51107
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05364944

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