N-chloro-succinimide in dichloromethane; toluene

1: 1) N-chlorosuccinimide (NCS) / 1) dichloromethane, -10 deg C, 10 min, 2) dichloromethane, -55 deg C to r.t. 2: toluene / 0.33 h / Heating View Scheme

potassium hydroxide in ethanol 8 h; Heating;

1: 97 percent / sodium periodate / methanol; H2O / 3 h / Ambient temperature 2: 97 percent / trifluoroacetic acid / CH2Cl2 / 1.83 h / Ambient temperature 3: iodine, triphenylphosphine, sodium iodide / acetonitrile / 0.08 h View Scheme

1: 97 percent / sodium periodate / methanol; H2O / 3 h / Ambient temperature 2: 97 percent / trifluoroacetic acid / CH2Cl2 / 1.83 h / Ambient temperature 3: iodine, triphenylphosphine, sodium iodide / acetonitrile / 0.08 h 4: 84 percent / xylene / 20 h / Heating View Scheme

1: 97 percent / sodium periodate / methanol; H2O / 3 h / Ambient temperature 2: 97 percent / trifluoroacetic acid / CH2Cl2 / 1.83 h / Ambient temperature 3: iodine, triphenylphosphine, sodium iodide / acetonitrile / 0.08 h 4: 84 percent / xylene / 20 h / Heating 5: 77 percent / sodium hydroxide / ethanol; H2O / 8 h / Heating View Scheme