1: 90 percent / SOCl2 / 2.5 h / Heating 2: 83 percent / diethyl ether / 3 h / -20 - 20 °C View Scheme

1: 1.) SOCl2 / 1.) 150 deg C, 1 h; 2.) benzene 4-5 h 2: 80 percent / LiAlH4 / diethyl ether / 15 h / Heating 3: 1 M NaOCl / CH2Cl2 / 1.5 h 4: 92 percent / 15 percent TiCl3 / acetic acid; H2O / -10 °C 5: methanol / 8 h / Heating View Scheme