1: 73 percent / HIO4 / H2O; 2-methyl-propan-2-ol / 5 h 2: 0.92 mg / hydroxylamine hydrochloride, aq. NaOH / ethanol / 0.17 h / 100 °C 3: 87 percent / H2 / PtO2 / methanol / 1.5 h / 2280 Torr View Scheme

1: 73 percent / HIO4 / H2O; 2-methyl-propan-2-ol / 5 h 2: 0.92 mg / hydroxylamine hydrochloride, aq. NaOH / ethanol / 0.17 h / 100 °C 3: 45 percent / nickel acetate tetrahydrate, piperidine / xylene / 24 h / 110 - 115 °C 4: 75 percent / bromine / methanol / 0.25 h / 70 - 80 °C 5: 34 percent / aq. NaOH / ethanol / 17 h / Heating View Scheme

periodic acid in water; tert-butyl alcohol 5 h;