Ethylene carbonate → 2-(4-Bromo-2,6-dimethylphenoxy)ethanol

HRID 580960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580960
[H-].[Li+].[Br:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[C:6]([CH3:12])[CH:5]=1.[H][H].C1(=O)O[CH2:18][CH2:17][O:16]1>CN(C=O)C>[Br:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11][CH2:18][CH2:17][OH:16])=[C:6]([CH3:12])[CH:5]=1

Komponenten

6

Edukt 4

HCID 7303Ethylene carbonateHCID 169194-Bromo-2,6-dimethylphenolHCID 62714Lithium hydrideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 537074432-(4-Bromo-2,6-dimethylphenoxy)ethanolAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Lithium hydride (200 mg) was added to a stirred solution of 4-bromo-2,6-dimethylphenol (65 g) in DMF at ambient temperature. When evolution of hydrogen had ceased, ethylene carbonate (31.9 g) was added and the mixture was heated at 150° C. for 12 hours. The DMF was removed by evaporation and the cooled residue was dissolved in ethyl acetate (500 ml). The ethyl acetate solution was washed with water (2×100 ml) and then with saturated brine (100 ml), dried (MgSO4) and evaporated. The residue was crystallised from methanol to give 2-(4-bromo-2,6-dimethylphenoxy)ethanol (51 g), m.p. 47-48° C. NMR (CDCl3): 2.21(6H,s), 3.86(2H,m), 3.93(2H,m), 7.12(2H,s).

Aufarbeitung

  1. customThe DMF was removed by evaporation
  2. dissolutionthe cooled residue was dissolved in ethyl acetate (500 ml)
  3. washThe ethyl acetate solution was washed with water (2×100 ml)
  4. dry with materialwith saturated brine (100 ml), dried (MgSO4)
  5. customevaporated
  6. customThe residue was crystallised from methanol

Quellen und Nachweise

ORD-Eintrag
ord-06e81898d9a141c3857cc9c903700f23
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919793

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