Octabenzone → 2(Benzotriazol2yl)4tert-octyl-6-(2hydroxy-3-benzoyl-6-n-octyloxybenzyl)phenol

HRID 1756469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756469
[Na].[OH:2][C:3]1[C:8]([CH2:9]N(CC)CC)=[CH:7][C:6]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:16])=[CH:5][C:4]=1[N:23]1[N:27]=[C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]2=[N:24]1.[OH:32][C:33]1[CH:46]=[C:45]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH:44]=[CH:43][C:34]=1[C:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:36].C[O-].[Na+]>CO>[N:24]1[N:23]([C:4]2[CH:5]=[C:6]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:16])[CH3:17])[CH:7]=[C:8]([CH2:9][C:46]3[C:45]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:44][CH:43]=[C:34]([C:35](=[O:36])[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:33]=3[OH:32])[C:3]=2[OH:2])[N:27]=[C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=12

Komponenten

6

Edukt 4

HCID 15797OctabenzoneHCID 5360545Sodium2×HCID 10942334Sodium MethoxideHCID 152194142-(2-Hydroxy-3-diethylaminomethyl-5-tert-octylphenyl)-2H-benzotriazole

Produkt 1

HCID 199172672(Benzotriazol2yl)4tert-octyl-6-(2hydroxy-3-benzoyl-6-n-octyloxybenzyl)phenolAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel4×

Versuchsvorschrift

Methanol (50 ml) is placed into a 300 ml three-necked flask equipped with a stirrer, thermometer, condenser, Dean-Stark trap and nitrogen inlet. Sodium (0.3 g, 0.013 mol) is added to the methanol and the mixture stirred at room temperature till all the sodium is dissolved. Then, 2-(2-hydroxy-3-diethylaminomethyl-5-tert-octylphenyl)-2H-benzotriazole (10.2 g, 0.025 mol), 2-hydroxy-4-n-octyloxybenzophenone (8.2 g, 0.025 mol) and another 50 ml of methanol are added to the sodium methoxide solution. The reactants are heated at reflux till half the methanol is collected in the Dean-Stark trap. o-Xylene (50 ml) is added and the temperature is raised to the reflux temperature of o-xylene (143°-145° C.) and heating is continued for 24 hours. The mixture is then cooled and acetic acid is added to neutralize the sodium methoxide catalyst. The o-xylene solvent is then removed by vacuum distillation. The crude product obtained is recrystallized from heptane to afford the title compound in a yield of 10 g (62 % yield) as a white crystalline solid melting at 96°-100° C.

Aufarbeitung

  1. customequipped with a stirrer
  2. dissolutionis dissolved
  3. temperatureThe reactants are heated
  4. customis collected in the Dean-Stark trap
  5. additiono-Xylene (50 ml) is added
  6. temperaturethe temperature is raised to the reflux temperature of o-xylene (143°-145° C.)
  7. temperatureheating
  8. temperatureThe mixture is then cooled
  9. additionacetic acid is added
  10. customThe o-xylene solvent is then removed by vacuum distillation
  11. customThe crude product obtained
  12. customis recrystallized from heptane

Quellen und Nachweise

ORD-Eintrag
ord-c7c2b6cc19c040ddbb04ca435116aa01
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05439955

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