1: 1.) Et3SiH, BF3-Et2O, 2.) H2 / 1.) methylene dichloride, 0 deg C, 1 h, 2.) Pd/C, RT, 45-50 psi, 20 h 2: 73 percent / aq. NaOH / methanol / 1 h / Heating View Scheme

potassium hydroxide in methanol T=40°C; 4 h; Inert atmosphere;

1: 1.) Et3SiH, BF3-Et2O, 2.) H2 / 1.) methylene dichloride, 0 deg C, 1 h, 2.) Pd/C, RT, 45-50 psi, 20 h 2: 73 percent / aq. NaOH / methanol / 1 h / Heating 3: 100 percent / SOCl2 / 3 h / 80 °C 4: 92 percent / AlCl3 / benzene / 1.5 h / Heating View Scheme

1: 1.) Et3SiH, BF3-Et2O, 2.) H2 / 1.) methylene dichloride, 0 deg C, 1 h, 2.) Pd/C, RT, 45-50 psi, 20 h 2: 73 percent / aq. NaOH / methanol / 1 h / Heating 3: 100 percent / SOCl2 / 3 h / 80 °C View Scheme