3,5-Di-tert-butylphenol → 2-(1-Aminoethyl)-3,5-di-tert-butylphenol

HRID 1173305

Reaction equation

HRID 1173305 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(O[CH:20]([NH:22]C(=O)C)[CH3:21])(C)C>FC(F)(F)C(O)=O>[NH2:22][CH:20]([C:8]1[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=1[OH:15])[CH3:21]

Participants

4

Reactant 2

HCID 708253,5-Di-tert-butylphenolHCID 14204909N-(1-Isopropoxyethyl)acetamide

Product 1

HCID 104672612-(1-Aminoethyl)-3,5-di-tert-butylphenol

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2.06 g (10.0 mmol) of 3,5-di-tert-butylphenol in 10 mL of trifluoroacetic acid was added 1.6 g (11.0 mmol) of N-(1-isopropoxyethyl)acetamide and the resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layers were separated and then extracted with EtOAc. The organic layers were combined, dried (Na2SO4), filtered and evaporated in vacuo. The product was purified on a silica gel flash chromatography column eluted with 0-25% EtOAc in CH2Cl2. Evaporation of the purified fraction and drying in vacuo afforded the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. customThe aqueous layers were separated
  4. extractionextracted with EtOAc
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe product was purified on a silica gel flash chromatography column
  9. washeluted with 0-25% EtOAc in CH2Cl2
  10. customEvaporation of the purified fraction
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-ad47a43033f5478db11c66aea3474bbe
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Linked notes

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