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

HRID 868710Notes

Reaction equation

HRID 868710 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.C(=O)C.[N:39]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[N:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[CH3:53]O>O>[N+:1]([C:52]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[N:39]=[N:40][C:41]1[CH:46]=[C:45]([C:32]([CH2:33][C:34]([CH3:26])([CH3:22])[CH3:53])([CH3:31])[CH3:27])[CH:44]=[CH:43][C:42]=1[OH:20])([O-:3])=[O:2]

Participants

8

Reactant 6

HCID 177AcetaldehydeHCID 887MethanolHCID 2272AzobenzeneHCID 10241FluorenoneHCID 14798Sodium HydroxideHCID 740294-Methyl-2-[2-(2-nitrophenyl)diazenyl]phenol

Product 1

HCID 1039272-((2-Nitrophenyl)azo)-4-(1,1,3,3-tetramethylbutyl)phenol

Reagents, catalysts & solvents 1

HCID 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 mixture was stirred while raising temperature to 65° C. 9-fluorenone 1.2 g and then 90% acetoaldehyde 6.5 g were added to the mixture for 1 hour. The resultant mixture was then stirred at the boiling point (75° C.) 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). In order to conduct Process (c), the reaction liquor was further stirred at the boiling point for 5 hours, thus the N-oxide having disappeared to complete Process (c).

Sources & evidence

ORD record
ord-4f0ecc925cc544e381d9c6ca4e971a83
Source dataset
uspto-grants-1988_10
Patent number
US04780541

Reaction notes

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