sodium hydroxide in methanol; water

aluminium trichloride T=10 - 15°C; 1 h;

aluminium trichloride in dichloromethane T=20°C; Friedel-Crafts acylation;

aluminium trichloride in dichloromethane 15 h; Ambient temperature;

1: NaH / 1) THF, 20-45 deg C, overnight, ultrasonic bath, 2) THF, 0 deg C, 3) reflux, 5 h 2: 1) Li, 2) p-benzoquinone / 1) THF, 5-10 deg C, 4 h, ultrasonic bath, 2) 45 deg C, overnight, 3) H2CCl2, 0 deg C, 3 h 3: 90 percent / methanol / 0.08 h / Heating 4: NaH / 1) 20-40 deg C, THF, 2) THF, -78 deg C, 3) room temperature, 1 h 5: 46 percent / AlCl3 / CH2Cl2 / 15 h / Ambient temperature View Scheme

1: 1) Li, 2) p-benzoquinone / 1) THF, 5-10 deg C, 4 h, ultrasonic bath, 2) 45 deg C, overnight, 3) H2CCl2, 0 deg C, 3 h 2: 90 percent / methanol / 0.08 h / Heating 3: NaH / 1) 20-40 deg C, THF, 2) THF, -78 deg C, 3) room temperature, 1 h 4: 46 percent / AlCl3 / CH2Cl2 / 15 h / Ambient temperature View Scheme

1: 90 percent / methanol / 0.08 h / Heating 2: NaH / 1) 20-40 deg C, THF, 2) THF, -78 deg C, 3) room temperature, 1 h 3: 46 percent / AlCl3 / CH2Cl2 / 15 h / Ambient temperature View Scheme

1: NaH / 1) 20-40 deg C, THF, 2) THF, -78 deg C, 3) room temperature, 1 h 2: 46 percent / AlCl3 / CH2Cl2 / 15 h / Ambient temperature View Scheme