2,4-Dichlorophenol → (2,4-Dichlorophenoxy)propanol

HRID 1654449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654449
Br[CH2:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[OH:14].N12CCCN=C1CCCCC2>C(O)(C)C.C(Cl)Cl>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[O:14][CH2:2][CH2:3][CH2:4][OH:5]

Komponenten

6

Edukt 3

HCID 84492,4-DichlorophenolHCID 123083-Bromo-1-propanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 1

HCID 235019(2,4-Dichlorophenoxy)propanolAusbeute 105,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-bromopropanol (53.86 g, 0.368 mol) in isopropanol is added dropwise to a mixture of 2,4-dichlorophenol (50 g, 0.307 mol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (70.05 g, 0.406 mol) in isopropanol at reflux. The reaction mixture is heated at reflux for 3 hours and concentrated in vacuo to obtain a residue. The residue is dissolved in methylene chloride and the organic solution is washed sequentially with 0.5N sodium hydroxide solution, 1M hydrochloric acid and brine, dried over MgSO4 and concentrated in vacuo to obtain an oil which solidifies to give the title product as a white solid (71.9 g, mp 53°-55° C.).

Aufarbeitung

  1. temperatureat reflux
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 3 hours
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue
  6. washthe organic solution is washed sequentially with 0.5N sodium hydroxide solution, 1M hydrochloric acid and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto obtain an oil which

Quellen und Nachweise

ORD-Eintrag
ord-44e71e535fee4b1088a7230e8a2bbd29
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05407897

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