Formaldehyde → 2-(2-hydroxy-5-methylphenyl)benztriazole N-oxide

HRID 868706Notes

Reaction equation

HRID 868706 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]([CH3:18])[CH:15]=[CH:14][C:13]=1[OH:19])([O-])=[O:2].[OH-].[Na+].C1C2C(=O)C3C(=CC=CC=3)C=2C=CC=1.C=O.N(C1C=CC=CC=1)=NC1C=CC=CC=1>O.CO>[OH:19][C:13]1[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=1[N:11]1[N+:1]([O-:2])=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:10]1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 2272AzobenzeneHCID 10241FluorenoneHCID 14798Sodium HydroxideHCID 740294-Methyl-2-[2-(2-nitrophenyl)diazenyl]phenol

Product 1

HCID 132146462-(2-hydroxy-5-methylphenyl)benztriazole N-oxide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

2-nitro-2'-hydroxy-5'-methylazobenzene 12.9 g was added to a mixture of methanol 60 ml, water 30 ml and 97% sodium hydroxide 12.4 g, and the resultant mixure was stirred while raising temperature to 65° C. Thereafter, the mixture was cooled to 40° C., and 9-fluorenone 0.8 g and then 80% paraformaldehyde 2.1 g were added to the mixture for 1 hour. The resultant mixture was then heated to the boiling point (75° C.), and was stirred at the boiling point for 6 hours, thus almost all of the azobenzene having disappeared to produce 2-(2-hydroxy-5-methylphenyl)benzotriazole-N-oxide.

Workup

  1. temperatureThereafter, the mixture was cooled to 40° C.
  2. stirringwas stirred at the boiling point for 6 hours

Sources & evidence

ORD record
ord-dd399ea76dbf46e09808d8a03c612ca4
Source dataset
uspto-grants-1988_10
Patent number
US04780541

Reaction notes

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