3-chloro-benzenecarboperoxoic acid in dichloromethane T=0°C; 1 h;

1: 95.9 percent / KOH / ethane-1,2-diol / 1 h / 180 °C 2: 1.) PCl5, 2.) AlCl3 / 1.) CS2, room temp., 5 h., 2.) chloroform, room temp., 12 h. View Scheme

1: 95.9 percent / KOH / ethane-1,2-diol / 1 h / 180 °C 2: 1.) PCl5, 2.) AlCl3 / 1.) CS2, room temp., 5 h., 2.) chloroform, room temp., 12 h. 3: LiAlH4 / tetrahydrofuran / 5 h / Heating View Scheme

1: 1.) POCl3 / 1.) 0-5 deg C then room temp. 15 min., 2.) DMF, 4 h., 40 deg C 2: piperidine / benzene / 4 h / Heating 3: 73 percent / KOH / ethanol; H2O / 1.33 h / Heating View Scheme