1,3-Dibromopropane → 2-[4-(3-Bromopropoxy)phenyl]ethanol

HRID 900222

Reaktionsgleichung

Reaktionsgleichung von HRID 900222
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:17][CH2:18][CH2:19][CH2:20]Br>C(#N)C>[Br:17][CH2:18][CH2:19][CH2:20][O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 10393TyrosolHCID 11430Potassium Carbonate

Produkt 1

HCID 218806552-[4-(3-Bromopropoxy)phenyl]ethanolAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 4-hydroxyphenethyl alcohol (4.37 g, 31.0 mmol) and potassium carbonate (6.55 g, 47.0 mmol) in acetonitrile (62.0 mL) was added 1,3 dibromopropane (31.0 mL, 316 mmol). The reaction mixture was heated to 70° C. for 12 hours and then cooled to room temperature, filtered and concentrated under vacuum. The resulting oil was purified by silica gel chromatography using a mixture of 4:1 hexanes and ethyl acetate to give the title compound (6.21 g) as a white solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customThe resulting oil was purified by silica gel chromatography
  5. additiona mixture of 4:1 hexanes and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cabd3098ed874b72920ab60b6b22771f
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358244B2

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