Sodium Hydroxide → Octrizole

HRID 441518

Reaction equation

HRID 441518 reaction equation
OC1C(C(CC)(C)C)=CC(C(CC)(C)C)=CC=1N=NC1C=CC=CC=1[N+]([O-])=O.[OH:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:38])[CH3:37])=[CH:32][C:31]=1[N:44]=[N:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[N+:52]([O-])=O.[OH-].[Na+].[N+](C1C=CC=CC=1N=NC1C=CC=CC=1)([O-])=O>>[OH:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:38])[CH3:37])=[CH:32][C:31]=1[N:44]1[N:52]=[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]2=[N:45]1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 1039272-((2-Nitrophenyl)azo)-4-(1,1,3,3-tetramethylbutyl)phenolHCID 1041112-Nitro-2'-hydroxy-3',5'-bis(tert-amyl)azobenzeneHCID 142206Diazene, (nitrophenyl)phenyl-, (E)-

Product 1

HCID 62485OctrizoleYield 62.6%

Procedure

When in Example 1, the 2'-hydroxy-3',5'-di-tert-amyl-2-nitroazobenzene was replaced by an equivalent amount of 2'-hydroxy-5'-tert-octyl-2-nitroazobenzene and the moles of sodium hydroxide per mole of o-nitroazobenzene intermediate was increased from 0.42/1 to 1.2/1, the product 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole was obtained in an isolated yield of 62.6% of theory with a melting point of 104°-107° C. The mother liquor contained a compound believed to be an isomer of the desired product.

Sources & evidence

ORD record
ord-3ae049e8c8894710b33557fb527ff2e0
Source dataset
uspto-grants-1977_08
Patent number
US04041044

Linked notes

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