1: 1.) AlCl3, 2.) 1N NaOH / 1.) CH2Cl2, room temp., 2 h, 2.) 15 min 2: 1.) 1 N NaOH, Na2S2O4, 2.) air-O2 / 1.) CH3OH, reflux, 15 min View Scheme

thionyl chloride T=50°C; 0.5 h;

1: 87 percent / SOCl2 / 0.5 h / 50 °C 2: 93 percent / NaOC2H5 / ethanol / 1.5 h / 50 °C 3: 1 N NaOH / methanol / 0.75 h / Ambient temperature 4: 662 mg / 0.25 h / 130 °C 5: 1.) AlCl3, 2.) 1N NaOH / 1.) C6H6, 50 deg C, 5 h, 2.) 15 min View Scheme