1: 86 percent / NaOMe / diethyl ether / 24 h / Ambient temperature 2: 80 percent / KOH / ethanol; H2O / 6 h / Heating 3: 70 percent / urea / xylene / Heating 4: 58 percent / sodium bis(2-methoxyethoxy)aluminum hydride / benzene / 2 h / Heating View Scheme

1: 4-methyl-phenyl-acetyl chloride With N-bromosuccinmide; thionyl chloride; hydrogen bromide in water T=90°C; 1 h; 2: With thionyl chloride 0.75 h; Heating / reflux; 3: methanol T=20°C;

1: H2SO4 / Heating 2: NBS, AIBN / CCl4 / Heating View Scheme

N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane Heating; Yield given;

Yield given;

sodium methylate in diethyl ether 24 h; Ambient temperature;

1: 86 percent / NaOMe / diethyl ether / 24 h / Ambient temperature 2: 80 percent / KOH / ethanol; H2O / 6 h / Heating 3: 70 percent / urea / xylene / Heating 4: 58 percent / sodium bis(2-methoxyethoxy)aluminum hydride / benzene / 2 h / Heating 5: 44 percent / HCOOH / 3 h / 100 °C View Scheme