O-Xylene → 2-Hydroxy-2'nitro3,4'-diphenyl-5-tert-octylazobenzene

HRID 48565Notes

Reaction equation

[OH-].[Na+].[C:3]1([C:9]2[CH:14]=[C:13]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:16])[CH:12]=[CH:11][C:10]=2[OH:23])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S([O-])(O)(=O)=O.[C:29]1([C:35]2[CH:40]=[CH:39][C:38]([N+:41]#[N:42])=[C:37]([N+:43]([O-:45])=[O:44])[CH:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(C)C(C)=CC=CC=1>CO>[OH:23][C:10]1[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:14][C:13]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:16])[CH3:17])=[CH:12][C:11]=1[N:42]=[N:41][C:38]1[CH:39]=[CH:40][C:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:36][C:37]=1[N+:43]([O-:45])=[O:44]

Participants

Conditions

Temperature: 2.5 °C

Procedure

To a solution of sodium hydroxide (12 g, 0.3 mol) and 2-phenyl-4-tert-octylphenol (14.1 g, 0.05 mol) in 150 mL of methanol maintained at 0-5° C. is added portionwise over 1.25 hours 4-phenyl-2-nitrobenzenediazonium hydrogen sulfate (30.6 g, 0.065 mol), prepared in (C) above. The reaction mixture is stirred for two hours at 0-5° C. Xylene (200 mL) is added to the reaction mixture. The organic phase is separated and extracted with water (4×200 mL). The organic phase is filtered and the solvent removed by distillation under an atmosphere of nitrogen. The residue is purified by flash chromatography (90:10 heptane:ethyl acetate eluent) to give 6.56 g of the title compound as a viscous dark red liquid.

Workup

customThe organic phase is separated
extractionextracted with water (4×200 mL)
filtrationThe organic phase is filtered
customthe solvent removed by distillation under an atmosphere of nitrogen
customThe residue is purified by flash chromatography (90:10 heptane:ethyl acetate eluent)

Sources & evidence

ORD record: ord-73a3437641dc4385a539e0187fa3dcf8
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703510B2

Reaction notes

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