Toluene → 2-(2'-Hydroxy-3'5-di-tert-butylphenyl) benzotriazole

HRID 2082168

Reaktionsgleichung

Reaktionsgleichung von HRID 2082168
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[N:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:13]=1[OH:26])([O-])=O.C1(C)C=CC=CC=1.[OH-].[Na+].[H][H]>[C].[Pd].O.CC(O)C>[OH:26][C:13]1[C:14]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:15][C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:17][C:12]=1[N:11]1[N:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[N:1]1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 1041102,4-Bis(1,1-dimethylethyl)-6-[2-(2-nitrophenyl)diazenyl]phenolHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 774552-(2'-Hydroxy-3'5-di-tert-butylphenyl) benzotriazoleAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

35.5 g (0.1 mol) of 2-nitro-2'-hydroxy-3',5'-di-t-butylazobenzene, 0.125 g of 5% palladium carbon, 100 ml of toluene, 100 ml of IPA, 100 ml water and 8.3 g of caustic soda were charged into a 500-ml stainless autoclave equipped with an agitator. After the air in the autoclave had been replaced by hydrogen, the pressure of hydrogen was set to 10 kg/cm2. Reaction was effected in the same way as that employed in Example 1. After the reaction had been completed, the catalyst was filtered off. When part of the filtrate was subjected to quantitative analysis using GC, it was found that the yield of 2-(2'-hydroxy-3',5'-di-t-butylphenyl)benzotriazole is 82%. After the solvent had been distilled off from the filtrate, the residual solid was crystallized by IPA, washed with IPA and then dried to obtain 23.6 g of 2-(2'-hydroxy-3',5'-di-t-butylphenyl)benzotriazole (yield, 73%; melting point, 150° to 152° C.).

Aufarbeitung

  1. customequipped with an agitator
  2. customReaction
  3. filtrationthe catalyst was filtered off
  4. distillationAfter the solvent had been distilled off from the filtrate
  5. customthe residual solid was crystallized by IPA
  6. washwashed with IPA
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3d47e57f955241b7acc60e70a49c1ad4
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05187289

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