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

HRID 868707Notes

Reaction equation

HRID 868707 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]=[N:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[OH:21])([O-])=[O:4].C1C2C(=O)C3C(=CC=CC=3)C=2C=CC=1.C=O.N(C1C=CC=CC=1)=NC1C=CC=CC=1>C(O)C.O>[OH:21][C:15]1[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=1[N:13]1[N+:3]([O-:4])=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=[N:12]1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 2272AzobenzeneHCID 10241FluorenoneHCID 14797Potassium 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 702EthanolSolventHCID 962WaterSolvent

Procedure

95% potassium hydroxide 17.7 g was added and dissolved in a mixture of ethyl alcohol 80 ml and water 10 ml. 2-nitro-2'-hydroxy-5'-methylazobenzene 12.9 g was then added to the resultant solution at 50° to 60° C. for 30 minutes while stirring, and thereafter 9-fluorenone 0.6 g and 35% formalin 5.6 g were added to the solution in 30 minutes. The resultant mixture was stirred for 1 hour at 65° to 70° C., and was further reacted at the boiling point (85° C.) for 4 hours, thus almost all of the azobenzene having disappeared to produce 2-(2-hydroxy-5-methylphenyl)benzotriazole-N-oxide.

Workup

  1. customwas further reacted at the boiling point (85° C.) for 4 hours

Sources & evidence

ORD record
ord-4601cd0a238a42dbb3c6dd0150e027b6
Source dataset
uspto-grants-1988_10
Patent number
US04780541

Reaction notes

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