1: 70 percent / perchloric acid / H2O / 2 h / Ambient temperature 2: 1.) bromine, 2.) tributyltin hydride / 1.) carbontetrachloride, rt.; 2.) ether, reflux, 24 h. View Scheme

2-amino-phenol; chromium octoate T=224°C; 2.5 h;

2-amino-phenol; chromium octoate T=198 - 212°C; 1.5 h; Product distribution / selectivity;

aluminum oxide in toluene T=110°C; Rearrangement; Product distribution; Further Variations:CatalystsTemperatures;

1: 1) O3, 2) Me2S / 1) methanol, -65 - -70 deg C; 2) -78 deg C to r.t., 4 h 2: 82 percent / m-CPBA / CH2Cl2 / 60 h 3: 87 percent / zinc powder, NaI, sodium acetate, acetic acid / CH2Cl2 / 4 h / Ambient temperature 4: 88 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 5: 49 percent / pyridine / a) 0 deg C, 1.5 h; b) r.t., 6 h 6: NaN3 / dimethylformamide 7: LiAlH4 / diethyl ether 8: 70 percent / pyridine / CH2Cl2 / a) 0 deg C, 0.5 h; b) r.t., 8 h 9: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 10: 1) N,N-carbonyldiimidazole / 1) THF, r.t., 1 h; 2) r.t., 10 h 11: 93 percent / LiAlH4 / diethyl ether / 6 h / Heating View Scheme

With  perchloric acid in  water 2 h;  Ambient temperature;