4-Aminophenol → tert-Butyl 3-amino-4-hydroxybenzoate
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
Product 1
Reagents, catalysts & solvents 1
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 4Boc-aminophenol (20.1 g, 96%). MS(NH3—CI): (M+NH3+H)=227.