1: 98 percent / Et3N / CHCl3 / 2 h / 20 °C 2: 1.) N-chlorosuccinimide; 2.) Et3N / 1.) CCl4, 0 deg C, 2 h; 2.) CHCl3, reflux, 1.5 h, then 20 deg C, 12 h View Scheme

1: 59 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 2: 98 percent / Et3N / CHCl3 / 2 h / 20 °C 3: 1.) N-chlorosuccinimide; 2.) Et3N / 1.) CCl4, 0 deg C, 2 h; 2.) CHCl3, reflux, 1.5 h, then 20 deg C, 12 h View Scheme

N-chloro-succinimide; triethylamine 1.) CCl4, 0 deg C, 2 h; 2.) CHCl3, reflux, 1.5 h, then 20 deg C, 12 h; Yield given. Multistep reaction;

sodium periodate in methanol; water