Reaktion #76843

Reaktionsgleichung

( C )

4-Phenyl-2-nitrobenzenediazonium Hydrogen Sulfate

sodium hydroxide

2-phenyl-4-tert-octylphenol

Xylene

4-phenyl-2-nitrobenzenediazonium hydrogen sulfate

→

title compound

Ausbeute 25.8%

2-Hydroxy-2′nitro-3,4′-diphenyl-5-tert-octylazobenzene

Ausbeute 25.8%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic phase is separated
2. 2
   Extraktionextracted with water (4×200 mL)
3. 3
   FiltrationThe organic phase is filtered
4. 4
   Sonstigethe solvent removed by distillation under an atmosphere of nitrogen
5. 5
   SonstigeThe residue is purified by flash chromatography (90:10 heptane:ethyl acetate eluent)

Vorschrift

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.

Quelle