1: 1.) n-butyl-lithium / 1.) ether, 4 h, -15 deg C, 2.) 2 h, -15 deg C 2: 69.3 percent / glacial acetic acid, 20percent H2SO4 / H2O / 2 h / 120 °C View Scheme

water 1) ether, RT; Yield given. Multistep reaction;

1: 78 percent / alumina / 7 h / Ambient temperature 2: 1.) lithium methylate, 2.) sodium tetraborate, KMnO4 / 1.) methanol, 0-2 deg C, 15 min, 2.) water, room temperature, 30 min View Scheme

1: 67 percent / TiCl4, H2O, MeOH 2: 1.) 2-methoxybenzoyl chloride View Scheme

2-methoxy-benzoyl chloride Yield given. Multistep reaction;

sodium hydroxide in ethanol

1: 82.3 percent / boron trifluoride etherate / CH2Cl2 / 2 h / Ambient temperature 2: 1.) sodium hydride / 1,2-dimethoxy-ethane / 1.) 0.5 h, 70 deg, 2.) 1 h, reflux 3: 79.5 percent / sodium borohydride / methanol / 1 h / Ambient temperature 4: 44.3 percent / pyridine / 8 h / Ambient temperature 5: 33.6 percent / lithium bromide / dimethylformamide / 5 h / 80 °C 6: 78.7 percent / methyl iodide / H2O; acetone / 5 h / Heating View Scheme