Water → 2-(4-Bromo-2-methylphenyl)ethanol

HRID 734899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734899
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](OC(C)(C)C)=[O:16])=[C:10]([CH3:22])[CH:9]=1.O.[OH-].[Na+]>C1COCC1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[C:10]([CH3:22])[CH:9]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67335992Tert-butyl (4-bromo-2-methylphenyl)acetate

Produkt 1

HCID 578428522-(4-Bromo-2-methylphenyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6.31 mL (6.31 mmol, 1M solution in THF) of lithium aluminum hydride was added at −5° C. to a solution of 4.00 g (6.31 mmol) of tert-butyl (4-bromo-2-methylphenyl)acetate in 50 mL of THF. The reaction mixture was heated to RT and stirred at this temperature until the reaction was complete. 0.3 mL of water, 0.3 mL of 15% aqueous sodium hydroxide solution, and 0.9 mL of water were added successively. After filtration, the organic phase was dried over magnesium sulfate and the solvent was eliminated in vacuo. Further purification was carried out by column chromatography on silica gel (PE/EtOAc 8:2). Yield: 1.02 g (75% of theoretical); C9H11BrO (M=215.087); calc.: molpeak (M)+:214/216 (Br); found: molpeak (M)+:214/216 (Br); Rf value: 0.59 (silica gel, PE/EtOAc 8:2).

Aufarbeitung

  1. filtrationAfter filtration
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. customFurther purification

Quellen und Nachweise

ORD-Eintrag
ord-e52b222864044a92b967b6fbf710e485
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592358B2

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