1-iso-propyl-4-methylbenzene; sodium in xylene

chromic acid in acetic acid

osmium(VIII) oxide in pyridine 96 h; Ambient temperature; Yield given. Yields of byproduct given;

1: 1) NaOH, NaNO2, 10percent HCl, 2) NH2OH, Cu(2+) / 1) water, 0 deg C, 30 min, 2) reflux 2: 80 percent 3: Na / toluene 4: H2O, H(1+) View Scheme

1: H2O2, NaOH 2: 1) NaOH, NaNO2, 10percent HCl, 2) NH2OH, Cu(2+) / 1) water, 0 deg C, 30 min, 2) reflux 3: 80 percent 4: Na / toluene 5: H2O, H(1+) View Scheme

1: 86percent H2SO4 / 1) 55 deg C, 10 min, 2) 75 deg C, 30 min 2: H2O2, NaOH 3: 1) NaOH, NaNO2, 10percent HCl, 2) NH2OH, Cu(2+) / 1) water, 0 deg C, 30 min, 2) reflux 4: 80 percent 5: Na / toluene 6: H2O, H(1+) View Scheme