Azobenzene → 2-(2-hydroxy-5-t-butylphenyl)benzotriazole-N-oxide

HRID 2166264Notes

Reaction equation

C1C2C(=O)C3C(=CC=CC=3)C=2C=CC=1.[OH-].[Na+].[N+:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]=[N:27][C:28]1[CH:33]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:31]=[CH:30][C:29]=1[OH:38])([O-])=[O:18].N(C1C=CC=CC=1)=NC1C=CC=CC=1>O.C(O)(CC)C>[OH:38][C:29]1[CH:30]=[CH:31][C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:33][C:28]=1[N:27]1[N+:17]([O-:18])=[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]2=[N:26]1

Participants

Conditions

Temperature: 80 °C

Procedure

9-fluorenone 2.5 g was added to a mixture of secondary butanol 80 g, water 14 g and 97% sodium hydroxide 22.4 g, and 2-nitro-2'-hydroxy-5'-t-butylazobenzene 19.9 g was added to the resultant mixture for one hour while stirring at 80° C. The mixture was further stirred at 90°~97° C. for 4 hours, thus almost all of the azobenzene having disappeared to produce 2-(2-hydroxy-5-t-butylphenyl)benzotriazole-N-oxide. Thus, the reaction of Process (b) was completed. The resultant reaction liquor was further stirred for 4 hours, thus the N-oxide having disappeared to finish the reaction of Process (c).

Workup

stirringThe mixture was further stirred at 90°~97° C. for 4 hours

Sources & evidence

ORD record: ord-a7d8209b94ae4cad8f47f05e00c7f730
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04943637

Reaction notes

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