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

HRID 401321Notes

Reaction equation

HRID 401321 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-ff0f2592b6f1475fa32756ad4428554c
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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