Formaldehyde → 2-((2-Nitrophenyl)azo)-4-(1,1,3,3-tetramethylbutyl)phenol

HRID 868709Notes

Reaction equation

[N+:1](C1C=CC=CC=1N=NC1C=C(C)C=CC=1O)([O-:3])=[O:2].[OH-:20].[Na+].[CH:22]1[C:34]2[C:33](=O)[C:32]3[C:27](=CC=C[CH:31]=3)[C:26]=2C=CC=1.[CH2:36]=O.[N:38]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[N:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O.CO>[N+:1]([C:51]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[N:38]=[N:39][C:40]1[CH:45]=[C:44]([C:32]([CH2:33][C:34]([CH3:26])([CH3:22])[CH3:36])([CH3:31])[CH3:27])[CH:43]=[CH:42][C:41]=1[OH:20])([O-:3])=[O:2]

Participants

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 (Process (b) having completed).

Workup

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

Sources & evidence

ORD record: ord-cd8034754d024ecdabb323ad40404cf7
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04780541

Reaction notes

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