Benzaldehyde → (2-Methyl-1-naphthyl)(phenyl)methanol

HRID 54972

Reaktionsgleichung

Reaktionsgleichung von HRID 54972
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:12].[Mg].[CH:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH3:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:21]

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 757541-Bromo-2-methylnaphthaleneHCID 5462224Magnesium

Produkt 1

HCID 19957120(2-Methyl-1-naphthyl)(phenyl)methanolAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 10 g (45 mmol) of 1-bromo-2-methylnaphthalene in 75 mL of THF was refluxed with 1.2 g (50 mmol) of magnesium turnings for three hours. The reaction was cooled on ice and 4.8 mL (43 mmol) of benzaldehyde was added. The ice was removed, the reaction was stirred 45 minutes and quenched with 5 mL of 1N HCl followed by 50 mL of water. The reaction was extracted into ethyl acetate, dried over sodium sulfate and flash chromatographed through silica gel with 5-10% ethyl acetate in hexane to provide 8.4 g (75%) of 2-methyl-a-phenyl-1-naphthalenemethanol as a pale yellow gum.

Aufarbeitung

  1. additionwas added
  2. customThe ice was removed
  3. customquenched with 5 mL of 1N HCl
  4. extractionThe reaction was extracted into ethyl acetate
  5. dry with materialdried over sodium sulfate and flash
  6. customchromatographed through silica gel with 5-10% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-0c4660183fbc41969b1652484277c365
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624922

Verknüpfte Notizen

Wird geladen…