2-Chloroethanol → 2-[4-(1H-1,2,4-Triazol-1-yl)phenoxy]ethanol

HRID 327642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 327642
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.Cl[CH2:14][CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:12][CH2:14][CH2:15][OH:16])=[CH:10][CH:11]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Komponenten

5

Edukt 3

HCID 342-Chloroethanol2×HCID 11430Potassium CarbonateHCID 1100644-(1,2,4-Triazol-1-yl)phenol

Produkt 1

HCID 191086732-[4-(1H-1,2,4-Triazol-1-yl)phenoxy]ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A stirred mixture of 4(1H-1,2,4-triazol-1-yl)phenol (16.1 g, 0.10 mole), 2-chloroethanol (25.5 g, 0.30 mole), potassium carbonate (42 g, 0.30 mole) and methyl ethyl ketone (100 ml) was heated at reflux temperature for 10 hr. An additional 16.1 g (0.20 mole) of 2-chloroethanol was added to the reaction mixture and heating at reflux temperature continued for another 24 hr. The hot mixture was filtered and the filtrate chilled. The crystalline precipitate was collected by filtration and the filter cake rinsed with water to remove most of the dark color. The solid was triturated with hot ethyl acetate, the mixture cooled, and the light tan crystals collected to yield 14.0 g (68%); mp 151°-152° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux temperature for 10 hr
  3. temperatureheating
  4. temperatureat reflux temperature
  5. filtrationThe hot mixture was filtered
  6. temperaturethe filtrate chilled
  7. filtrationThe crystalline precipitate was collected by filtration
  8. washthe filter cake rinsed with water
  9. customto remove most of the dark color
  10. customThe solid was triturated with hot ethyl acetate
  11. temperaturethe mixture cooled
  12. customthe light tan crystals collected
  13. customto yield 14.0 g (68%)

Quellen und Nachweise

ORD-Eintrag
ord-926abf54928b495c941c665097d8b65d
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273993

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