Hydrochloric Acid → 2,6-Di-t-butyl-4-(2-nitrophenyl)phenol

HRID 1380711Notes

Reaction equation

[OH-].[Na+].[N+]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])([O-])=O.[C:15]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:20]=1[OH:29])([CH3:18])([CH3:17])[CH3:16].Cl>CS(C)=O>[C:25]([C:21]1[CH:22]=[C:23]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N+:12]([O-:14])=[O:13])[CH:24]=[C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:20]=1[OH:29])([CH3:28])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 30 mg (0.75 mmol) of powdered sodium hydroxide, 100 mg (0.59 mmol) of 1,2-dinitrobenzene, 155 mg (0.75 mmol) of 2,6-di-t-butylphenol, and 1.0 mL of dimethylsulfoxide was heated at 60° C. for 17 hours and poured into 10 mL of 1N HCl, and the resulting aqueous mixture was extracted with three 10 mL portions of diethyl ether. The ether layers were combined, dried over magnesium sulfate, and concentrated. Purification of the residue by preparative thin layer chromatography (tlc) afforded 206 mg of crude 2,6-di-t-butyl-4-(2-nitrophenyl)phenol.

Workup

extractionthe resulting aqueous mixture was extracted with three 10 mL portions of diethyl ether
dry with materialdried over magnesium sulfate
concentrationconcentrated
customPurification of the residue by preparative thin layer chromatography (tlc)

Sources & evidence

ORD record: ord-dfff3ea9b801490187e44673035ef8ed
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04582947

Reaction notes

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