Hydrochloric Acid → HCID 13466713, compound

HRID 485950Notes

Reaction equation

HRID 485950 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)([O-:5])=[O:4].[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:9]2[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][C:8]=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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74521,3-DinitrobenzeneHCID 14798Sodium HydroxideHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 13466713HCID 13466713, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 30 mg (0.75 mmol) of powdered sodium hydroxide, 100 mg (0.59 mmol) of 1,3-dinitrobenzene, 155 mg (0.75 mmol) of 2,6-di-t-butylphenol, and 1.0 mL of dimethylsulfoxide was heated at 80° C. for one hour 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 (PTLC) and crystallization afforded 89 mg (40% yield) of 2,6-di-t-butyl-4-(2',4'-dinitrophenyl)phenol.

Workup

  1. extractionthe resulting aqueous mixture was extracted with three 10 mL portions of diethyl ether
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customPurification of the residue
  5. customby preparative thin layer chromatography (PTLC) and crystallization

Sources & evidence

ORD record
ord-dd62b14da41b430a9b0d07bafabbea02
Source dataset
uspto-grants-1985_08
Patent number
US04538006

Reaction notes

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