Sodium Hydroxide → UV-328

HRID 1030320Notes

Reaction equation

HRID 1030320 reaction equation
[OH:1][C:2]1[C:7]([C:8]([CH2:11][CH3:12])([CH3:10])[CH3:9])=[CH:6][C:5]([C:13]([CH2:16][CH3:17])([CH3:15])[CH3:14])=[CH:4][C:3]=1[N:18]1[N+:22]([O-])=[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]2=[N:19]1.[OH-].[Na+].[H][H]>[Ni].O>[OH:1][C:2]1[C:7]([C:8]([CH2:11][CH3:12])([CH3:10])[CH3:9])=[CH:6][C:5]([C:13]([CH2:16][CH3:17])([CH3:15])[CH3:14])=[CH:4][C:3]=1[N:18]1[N:22]=[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]2=[N:19]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 111431102-(2H-Benzotriazol-2-yl)-4,6-bis(tert-pentyl)phenol N-oxideHCID 178418361HCID 178418361, compound3×

Product 1

HCID 33263UV-328Yield 90.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

36.7 g (0.1 mol) of 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzotriazole-N-oxide, 150 ml of water, 8 g (0.2 mol) of caustic soda and 5 g of Raney nickel 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 After the air in the autoclave had been replaced by hydrogen, the pressure of hydrogen was set to 10 kg/cm2. The temperature of the resultant mixture was increased under agitation to 90° C. at which the mixture was then subjected to reaction for 8 hours until the absorption of hydrogen was stopped. After the reaction had been completed, the autoclave was cooled, and the catalyst was filtered off. The filtrate was then allowed to stand to separate an upper toluene layer. Most part of toluene layer was distilled off, and the resultant residual solid was crystallized from IPA and then dried to obtain 31.7 g of 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzotriazole (yield, 90.3%; melting point, 78° to 80° C.).

Workup

  1. customequipped with an agitator
  2. temperaturethe autoclave was cooled
  3. filtrationthe catalyst was filtered off
  4. customto separate an upper toluene layer
  5. distillationMost part of toluene layer was distilled off
  6. customthe resultant residual solid was crystallized from IPA
  7. customdried

Sources & evidence

ORD record
ord-a47535ba496f4d7cbd20bcd85c301a45
Source dataset
uspto-grants-1992_04
Patent number
US05104992

Reaction notes

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