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

HRID 2166260Notes

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>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

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 mixture 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 to produce 2-(2-hydroxy-3,5-di-t-amylphenyl)benzotriazole-N-oxide. Thus, the reaction of Process (b) was finished.

Workup

temperatureThereafter, the mixture was cooled to 50° C.
temperatureThe reaction mixture was then heated to 90° C. in one hour
customreaction

Sources & evidence

ORD record: ord-476de73c9644423da54a11e78a43ff52
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04943637

Reaction notes

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