Sodium Hydroxide → 2-Hydroxy-2'nitro-3-alpha-cumyl-4'-phenyl-5-tert-octylazobenzene

HRID 48567Notes

Reaction equation

HRID 48567 reaction equation
OC1C(C2C=CC=CC=2)=CC(C(CC(C)(C)C)(C)C)=CC=1N=NC1C=CC(C2C=CC=CC=2)=CC=1[N+]([O-])=O.[OH-].[Na+].S([O-])(O)(=O)=O.[C:46]1([C:52]2[CH:57]=[CH:56][C:55]([N+:58]#[N:59])=[C:54]([N+:60]([O-:62])=[O:61])[CH:53]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[C:63]([C:72]1[CH:77]=[C:76]([C:78]([CH2:81][C:82]([CH3:85])([CH3:84])[CH3:83])([CH3:80])[CH3:79])[CH:75]=[CH:74][C:73]=1[OH:86])([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)([CH3:65])[CH3:64]>CO>[OH:86][C:73]1[C:72]([C:63]([C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=2)([CH3:65])[CH3:64])=[CH:77][C:76]([C:78]([CH2:81][C:82]([CH3:85])([CH3:84])[CH3:83])([CH3:80])[CH3:79])=[CH:75][C:74]=1[N:59]=[N:58][C:55]1[CH:56]=[CH:57][C:52]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[CH:53][C:54]=1[N+:60]([O-:62])=[O:61]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 22644018Phenol, 2-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)-HCID 858226914-Phenyl-2-nitrobenzenediazonium hydrogen sulfateHCID 1363776762-Hydroxy-2'nitro3,4'-diphenyl-5-tert-octylazobenzene

Product 1

HCID 1356781452-Hydroxy-2'nitro-3-alpha-cumyl-4'-phenyl-5-tert-octylazobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The procedure of Example 1 (D) is followed using sodium hydroxide (4 g, 0.1 mol), methanol (100 mL), 4-phenyl-2-nitrobenzenediazonium hydrogen sulfate (16 g, 0.034 mol) and 2-α-cumyl-4-tert-octylphenol (8.1 g, 0.028 mol) to give the title compound as a dark red solid melting at 176-179° C.

Sources & evidence

ORD record
ord-f24e6e9e99bd4fac890556b12ca9beb8
Source dataset
uspto-grants-2004_03
Patent number
US06703510B2

Reaction notes

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