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Hydrochloric Acid → 2,6-Di-t-butyl-4-(3'-cyano-4'-nitrophenyl)phenol

HRID 1719661
Notes
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Reaction equation

HRID 1719661 reaction equation
[OH-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])#[N:4].[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:19]=1[OH:28])([CH3:17])([CH3:16])[CH3:15].Cl>CS(C)=O>[C:24]([C:20]1[CH:21]=[C:22]([C:9]2[CH:8]=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[C:5]([C:3]#[N:4])[CH:10]=2)[CH:23]=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:19]=1[OH:28])([CH3:27])([CH3:26])[CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11922o-NitrobenzonitrileHCID 14798Sodium HydroxideHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 134667172,6-Di-t-butyl-4-(3'-cyano-4'-nitrophenyl)phenolYield 24.5%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of 30 mg (0.75 mmol) of powdered sodium hydroxide, 87 mg (0.59 mmol) of 2-cyano-1-nitrobenzene, 155 mg (0.75 mmol) of 2,6-di-t-butylphenol, and 1.0 mL of dimethylsulfoxide was heated at 80° C. for two 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 and crystallization afforded 51 mg (24% yield) of 2,6-di-t-butyl-4-(3'-cyano-4'-nitrophenyl)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 and crystallization

Sources & evidence

ORD record
ord-588db222e8484d6c85faa94fdc906d26
Source dataset
uspto-grants-1985_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04541962

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes