Sulfuric Acid → 2-(2H-Benzotriazol-2-yl)-4,6-bis(tert-pentyl)phenol N-oxide

HRID 2166254Notes

Reaction equation

HRID 2166254 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]=1O)([O-:3])=O.[OH-].[Na+].C1C2C(=[O:44])C3C(=CC=CC=3)C=2C=CC=1.N(C1C=CC=CC=1)=NC1C=CC=CC=1.S(=O)(=O)(O)O>O.C(O)CCC>[OH:44][C:13]1[C:14]([C:23]([CH2:26][CH3:27])([CH3:24])[CH3:25])=[CH:15][C:16]([C:18]([CH2:21][CH3:22])([CH3:19])[CH3:20])=[CH:17][C:12]=1[N:11]1[N+:1]([O-:3])=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:10]1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 2272AzobenzeneHCID 10241FluorenoneHCID 14798Sodium HydroxideHCID 1041112-Nitro-2'-hydroxy-3',5'-bis(tert-amyl)azobenzene

Product 1

HCID 111431102-(2H-Benzotriazol-2-yl)-4,6-bis(tert-pentyl)phenol N-oxideYield 568.8%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

2-nitro-2'-hydroxy-3',5'-di-t-amylazobenzene 25.5 g was added to a mixture of n-butanol 80 g, water 14 g and 97% sodium hydroxide 8.2 g, and the resultant mixure was stirred while raising temperature to 65° C. Thereafter, the mixture was cooled to 50° C., and 9-fluorenone 2.0 g was added to the mixture. The reaction mixture was then heated to 90° C. in one hour, and the mixture was stirred at 90°~96° C. for four hours to effect reaction, thus almost all of the azobenzene having disappeared. Thereafter, water 50 ml was added to the reaction liquor, and the reaction liquor was neutralized to pH 8~9 with 62% sulfuric acid 13 g to precipitate a crystal. The crystal thus obtained was filtered to separate the crystal, and the separated crystal was then fully washed with water and further with a small amount of methanol. The washed crystal was then dried, thus producing 23.2 g of 2-(2-hydroxy-3',5'-di-t-amylphenyl)benzotriazole-N-oxide having a melting point of 111° to 113° C. at the yield of 95.0%.

Workup

  1. temperatureThereafter, the mixture was cooled to 50° C.
  2. temperatureThe reaction mixture was then heated to 90° C. in one hour
  3. stirringthe mixture was stirred at 90°~96° C. for four hours
  4. customreaction
  5. customto precipitate a crystal
  6. customThe crystal thus obtained
  7. filtrationwas filtered
  8. customto separate the crystal
  9. washthe separated crystal was then fully washed with water and further with a small amount of methanol
  10. customThe washed crystal was then dried

Sources & evidence

ORD record
ord-86c5e57c3dee42e9b4e06bc61d6f6619
Source dataset
uspto-grants-1990_07
Patent number
US04943637

Reaction notes

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