Sodium Hydroxide → (2-Tert-butylphenyl)methanol

HRID 1620566

Reaktionsgleichung

Reaktionsgleichung von HRID 1620566
[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1.[OH-].[Na+]>C1COCC1>[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[CH2:7][OH:8])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 136850tert-Butylbenzoic acid (mixed isomers)HCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 19822435(2-Tert-butylphenyl)methanolAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-tert-butylbenzoic acid (1.00 g) in THF (20 mL) was added 1.0M borane THF complex THF solution (16.8 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight under a nitrogen atmosphere, 1N aqueous sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (942 mg).

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3d1f14f1598940cd8eab2f08def8b919
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772277B2

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