Stannous chloride dihydrate → 2-Amino-4,6-di-tert-butylphenol

HRID 423813Notes

Reaction equation

HRID 423813 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([N+:15]([O-])=O)[C:6]=1[OH:18])([CH3:4])([CH3:3])[CH3:2].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCO.CCOC(C)=O.O>[NH2:15][C:7]1[C:6]([OH:18])=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=1

Participants

7

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 6168972,4-Bis(tert-butyl)-6-nitrophenol

Product 1

HCID 3245552-Amino-4,6-di-tert-butylphenol

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,4-di-tert-butyl-6-nitro-phenol (27 mg, 0.11 mmol) and SnCl2.2H2O (121 mg, 0.54 mmol) in EtOH (1.0 mL) was heated in microwave oven at 100° C. for 30 min. The mixture was diluted with EtOAc and water, basified with sat. NaHCO3 and filtered through Celite. The organic layer was separated and dried over Na2SO4. Solvent was removed by evaporation to provide 6-amino-2,4-di-tert-butyl-phenol (C-8), which was used without further purification. HPLC ret. time 2.74 min, 10-99% CH3CN, 5 min run; ESI-MS 222.5 m/z (MH+).

Workup

  1. filtrationfiltered through Celite
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customSolvent was removed by evaporation

Sources & evidence

ORD record
ord-e5a671c3fca942dc8d579a2a60d33f7c
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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