1: 91 percent / conc. HCl / methanol / 15 h / Heating 2: 81 percent / MCPBA / CHCl3 / Ambient temperature 3: 1.) CuI / 1.) Et2O, -10 deg C, 20 min, 2.) Et2O, 0 deg C, 1 h 4: 68 percent / o-chloranil / toluene / Heating View Scheme

1: 91 percent / conc. HCl / methanol / 15 h / Heating 2: 81 percent / MCPBA / CHCl3 / Ambient temperature View Scheme

1: 91 percent / conc. HCl / methanol / 15 h / Heating 2: 81 percent / MCPBA / CHCl3 / Ambient temperature 3: 1.) CuI / 1.) THF, -15 deg C, 5 min, 2.) THF, RT, 24 h 4: 61 percent / o-chloranil / toluene / Heating View Scheme

1: 90 percent / conc. HCl / methanol / 15 h / Heating 2: 45 percent / CH3ONa / petroleum ether / 1.) 0 deg C, 2 h; 2.) RT, 15 h View Scheme