Sodium Dithionite → 4-Amino-2,6-di-tert-butylphenol

HRID 597122

Reaction equation

HRID 597122 reaction equation
[N:1]([C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([OH:13])=[C:5]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=1)=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>[OH-].[Na+].O>[NH2:1][C:3]1[CH:4]=[C:5]([C:14]([CH3:15])([CH3:16])[CH3:17])[C:6]([OH:13])=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:8]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 70383Phenol, 2,6-bis(1,1-dimethylethyl)-4-nitroso-

Product 1

HCID 3142204-Amino-2,6-di-tert-butylphenol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To 17.6 grams of 4-nitroso-2,6-di-tert-butylphenol dissolved in 60 ml of 5N sodium hydroxide and 120 ml of water was added with stirring over a 30-minute period a solution of 52.2 grams of sodium hydrosulfite in 220 ml of water during which time the temperature rose to 53° C. After the addition was complete, stirring was continued for another 2.5 hours. The product formed was then rapidly collected by filtration, washed with 400 ml of water and dried in a vacuum desiccator over phosphorus pentoxide to yield 4-amino-2,6-di-tert-butylphenol, melting at 105°-108° C.

Workup

  1. customrose to 53° C
  2. additionAfter the addition
  3. customThe product formed
  4. filtrationwas then rapidly collected by filtration
  5. washwashed with 400 ml of water
  6. dry with materialdried in a vacuum desiccator over phosphorus pentoxide

Sources & evidence

ORD record
ord-e6b888ac9faa4879afc7b26ca139e947
Source dataset
uspto-grants-1977_03
Patent number
US04013621

Linked notes

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