HCID 14940799, compound → 3-Aminophenyl 2,2-dimethylpropanoate

Participants

Reaction Steps

To 60 mL anhydrous CH2Cl2 was added O-pivaloyl-3-nitrophenol (5.0 g, 22.4 mmol) and a catalytic amount (50 mg) of 10% Pd on C. The flask was repeatedly evacuated and flushed with N2. The reaction flask was again evacuated and H2 was introduced by balloon. After stirring under an atmosphere of H2 for 3 h, the reaction flask was flushed twice with N2. The suspension was then filtered through a bed of Celite™ and concentrated to give 4.15 g (96%) of O-pivaloyl-3-aminophenol as a viscous amber oil. Data for O-pivaloyl-3-aminophenol: Rf 0.21 (silica gel, hexanes/EtOAc, 3:1); 1H NMR (400 MHz, CDCl3) 7.12 (dd, J=8.0, 8.0, 1 H), 6.52 (dd, J=7.8, 2.7, 1 H), 6.44 (ddd, J=8.0, 2.4, 1.4, 1H), 6.38 (t, J=2.2, 1 H), 3.81 (br s, 2 H), 1.34 (s, 9 H).

Provenance & Evidence