Water → (1-Phenyl-2-naphthyl)methanol

HRID 1451499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1451499
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[C:23](O)=[O:24])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C1COCC1.C(OCC)C>[C:7]1([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[CH2:23][OH:24])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

7

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 130428441-Phenylnaphthalene-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 19974716(1-Phenyl-2-naphthyl)methanolAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A 1.0M solution of lithium aluminiumhydride in THF (10 ml, 10 mmol) was placed under an atmosphere of nitrogen and a solution of 1-phenyl-2-naphthalenecarboxylic acid (2.4 g, 10 mmol, Synthesis 1983, 105) in dry THF (10 ml) was added dropwise. When addition was complete the mixture was stirred for 30 minutes at ambient temperature and then 30 minutes at reflux. The reaction mixture was allowed to cool and carefully water (0.4 ml), 4N sodium hydroxide (0.4 ml) and water (1.2 ml) were added successively. The mixture was stirred at ambient temperature for 30 minutes, diluted with diethylether and filtered. The solvent was evaporated in vacuo and the residue was dissolved in toluene. After drying (MgSO4) the solvent was evaporated in vacuo to give 2.3 g of crude (1-phenyl-2-naphthyl)methanol.

Aufarbeitung

  1. additionWhen addition
  2. temperature30 minutes at reflux
  3. temperatureto cool
  4. stirringThe mixture was stirred at ambient temperature for 30 minutes
  5. filtrationfiltered
  6. customThe solvent was evaporated in vacuo
  7. dissolutionthe residue was dissolved in toluene
  8. dry with materialAfter drying (MgSO4) the solvent
  9. customwas evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-273d677bd4da408c905889c351c53401
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604242

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