Carbon Dioxide → 2-[2'-Hydroxy, 4'-(2"-hydroxyethoxy)phenyl]benzotriazole

HRID 742610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 742610
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1.C1(=O)O[CH2:21][CH2:20][O:19]1.C(=O)=O>[Cl-].C[N+](C)(C)C.O>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:21][CH2:20][OH:19])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1

Komponenten

6

Edukt 3

HCID 280Carbon DioxideHCID 7303Ethylene carbonateHCID 110641672-(2,4-dihydroxyphenyl)-2H-benzotriazole

Produkt 1

HCID 229047232-[2'-Hydroxy, 4'-(2"-hydroxyethoxy)phenyl]benzotriazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6379Tetramethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

A mixture of 45.4 g (0.2 mole) of 2-(2',4'-dihydroxyphenyl)benzotriazole, 19.8 g (0.225 mole) of ethylene carbonate and 0.55 g (0.005 mole) of tetramethylammonium chloride was heated under argon while stirring in an oil bath. The mixture changed to a brown melt as the temperature rose to 140° C. The argon gas flow was stopped at this point and the temperature was raised to 155° C. After the evolution of carbon dioxide stopped (7-8 hours), the reaction mixture was cooled to about 100° C. and then within 5 minutes 150 mL of water was added while stirring. The mixture was cooled to room temperature while stirring, at which point the semi-solid looking product crystallized. After suctioning off the solid, washing with water, and drying; 2-[2'-hydroxy, 4'-(2"-hydroxyethoxy)phenyl]benzotriazole was obtained having purity of 98% (HPLC). Yield: 51.5 g (95% of the theoretical).

Aufarbeitung

  1. temperaturewas heated under argon
  2. customrose to 140° C
  3. custom(7-8 hours)
  4. temperaturethe reaction mixture was cooled to about 100° C.
  5. stirringwhile stirring
  6. temperatureThe mixture was cooled to room temperature
  7. stirringwhile stirring, at which point the semi-solid
  8. customcrystallized
  9. washwashing with water
  10. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-05d03d0f8a6c4a1ba2f2b03e0d6323fb
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554759

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