Toluene → UV-328

HRID 2082166Notes

Reaction equation

HRID 2082166 reaction equation
[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]([CH2:21][CH3:22])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:23]([CH2:26][CH3:27])([CH3:25])[CH3:24])[C:13]=1[OH:28])([O-])=O.C1(C)C=CC=CC=1.[OH-].[Na+].[H][H]>[Ni].O.C(O)(C)C>[OH:28][C:13]1[C:14]([C:23]([CH2:26][CH3:27])([CH3:25])[CH3:24])=[CH:15][C:16]([C:18]([CH2:21][CH3:22])([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

Participants

8

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 1041112-Nitro-2'-hydroxy-3',5'-bis(tert-amyl)azobenzeneHCID 178418361HCID 178418361, compound3×

Product 1

HCID 33263UV-328Yield 82%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

38.39 g (0.1 mol) of 2-nitro-2'-hydroxy-3',5'-di-t-amylazobenzene, 5 g of Raney nickel, 100 ml of toluene, 100 ml of isopropyl alcohol (referred to as "IPA" hereinafter) 100 ml of water and 8 g (0.2 mol) of caustic soda were charged into a 500-ml stainless autoclave with an agitator. After the air in the flask had been replaced by hydrogen, the pressure of hydrogen was set to 10 kg/cm2. The temperature was increased at a rate of 20° to 40° C./hour and then 40° to 50° C./hour while the resultant mixture being agitated. Reaction was then effected at 50° to 90° C. for 2 hours and then 90° C. for 7 hours and was stopped when no more hydrogen was absorbed by the reaction solution. The autoclave was cooled, and the catalyst was filtered off. After the filtrate had been allowed to stand, the toluene layer was separated, and most part of the toluene was distilled off. The residual solid obtained was crystallized by IPA and the dried to obtain 28.8 g of 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzotriazole (yield, 82%; melting point, 79° to 80° C.).

Workup

  1. temperatureThe temperature was increased at a rate of 20° to 40° C./hour
  2. customReaction
  3. wait90° C. for 7 hours
  4. customwas absorbed by the reaction solution
  5. temperatureThe autoclave was cooled
  6. filtrationthe catalyst was filtered off
  7. customthe toluene layer was separated
  8. distillationmost part of the toluene was distilled off
  9. customThe residual solid obtained
  10. customwas crystallized by IPA
  11. customthe dried

Sources & evidence

ORD record
ord-caccc19d3bee4cc18aba5e823a12a9f3
Source dataset
uspto-grants-1993_02
Patent number
US05187289

Reaction notes

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