4-Aminophenol → tert-Butyl 3-amino-4-hydroxybenzoate

HRID 2302018Notes

Reaction equation

HRID 2302018 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([O:16]C(OC(C)(C)C)=O)=O)([CH3:12])([CH3:11])[CH3:10].C([N:27](C(C)C)CC)(C)C>C1COCC1>[C:14]([C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([NH2:27])[CH:3]=1)([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:16]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 11160103tert-Butyl 3-amino-4-hydroxybenzoateYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-aminophenol (10.9 g, 100 mmol) in THF (150 mL) cooled in an ice bath was added di-tert-butyl-dicarbonate (21.8 g, 100 mmol) followed by diisopropylethylamine (17.4 mL, 100 mmol). The mixture was stirred at room temperature overnight and concentrated. The residue was taken up in ethyl acetate and the solution was washed with brine, dried (MgSO4), and concentrated. Purification on a silica gel column eluting with 5% methanol/40% ethyl acetate/hexane gave 4-Boc-aminophenol (20.1 g, 96%). MS(NH3-CI): (M+NH3+H)=227.

Workup

  1. concentrationconcentrated
  2. washthe solution was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification on a silica gel column
  6. washeluting with 5% methanol/40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6ddd1717bdbe4ab191f273578bfca1c3
Source dataset
uspto-grants-2002_08
Patent number
US06429213B1

Reaction notes

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