Diethyl Ether → (4'-Methyl(1,1'-biphenyl)-4-yl)methanol

HRID 1903713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903713
C[C:2]1([C:14]([O:16]C)=O)[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:33]COCC>C1COCC1>[CH3:33][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH2:14][OH:16])=[CH:7][CH:6]=2)=[CH:13][CH:12]=1

Komponenten

7

Edukt 5

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86738513Methyl 4-methyl[1,1-biphenyl]-4-carboxylate

Produkt 1

HCID 1394290(4'-Methyl(1,1'-biphenyl)-4-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Methyl-(1,1'-biphenyl)-4-carboxylic acid, methyl ester (1.43 g) in ether (25 ml) and THF (25 ml) was added over 5 min to LiAlH4 (420 mg) in ether (25 ml). The mixture was stirred at room temperature for 1 h and then cooled in ice. Aqueous NaOH (1 M, 2.1 ml) was added and after stirring (15 min) excess anhydrous Na2SO4 was added. The mixture was filtered and the filtrate evaporated to give a solid. Crystallisation from cyclohexane-methanol gave the title compound (1.04 g) m.p. 128°-31°.

Aufarbeitung

  1. temperaturecooled in ice
  2. additionwas added
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated
  5. customto give a solid
  6. customCrystallisation from cyclohexane-methanol

Quellen und Nachweise

ORD-Eintrag
ord-545c32b37da643fda45c8eda0236a6b0
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04438112

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