1-Chloro-4-nitrobenzene → 2,6-Ditert-butyl-4-(4-nitrophenyl)phenol

HRID 982152Notes

Reaction equation

[OH-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]=1[OH:17])([CH3:6])([CH3:5])[CH3:4].Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>CS(C)=O>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([C:11]2[CH:12]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:8]([OH:17])=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=2)=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 12.0 g (300 mmol) of powdered sodium hydroxide, 24.7 g (120 mmol) of 2,6-di-tert-butylphenol, 15.7 g (100 mmol) of 1-chloro-4-nitrobenzene, and 120 mL of DMSO was stirred for 17 hours at 90° C. and poured into one liter of IN HC1. The resulting aqueous mixture was extracted with three 250 mL portions of diethyl ether. Combination, drying (MgSO4), and concentration of the organic layers afforded a residue which was purified by two recrystallizations from ethanol-dichloromethane to give 22.3 g (68% yield) of 4-(4'-nitrophenyl)-2,6-di-tert-butylphenol which can also be named 3,5-bis-(1,1-dimethylethyl)-4'-nitro-(1,1'-biphenyl)-4ol.

Workup

additionpoured into one liter of IN HC1
extractionThe resulting aqueous mixture was extracted with three 250 mL portions of diethyl ether
dry with materialCombination, drying (MgSO4), and concentration of the organic layers
customafforded a residue which
customwas purified by two recrystallizations from ethanol-dichloromethane

Sources & evidence

ORD record: ord-712c36a8b4204b46a043e28e3b31a20e
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994545

Reaction notes

Loading…