1: 0.66 g / 1M NaOH, Bu4NHSO4 / benzene; H2O / 3 h / Heating 2: 27 percent / CH3ONa / dimethylformamide / 2 h / 40 °C 3: 84 percent / 1.5M NaOH, Bu4NHSO4, 2,6-di-t-butyl-4-methylphenol / H2O / 3 h / Heating 4: 86 percent / methanol / 16 h / 65 °C View Scheme

1: 0.66 g / 1M NaOH, Bu4NHSO4 / benzene; H2O / 3 h / Heating 2: 27 percent / CH3ONa / dimethylformamide / 2 h / 40 °C 3: 1.) NaH / 1.) DMF, 2.) 50 deg C View Scheme

sodium methylate; hydrogen cation Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

sodium ethanolate in ethanol 24 h; Heating;

sodium methylate; hydrogen cation Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1: 0.66 g / 1M NaOH, Bu4NHSO4 / benzene; H2O / 3 h / Heating 2: 27 percent / CH3ONa / dimethylformamide / 2 h / 40 °C 3: 84 percent / 1.5M NaOH, Bu4NHSO4, 2,6-di-t-butyl-4-methylphenol / H2O / 3 h / Heating 4: 94 percent / dimethylformamide / 1.5 h / 80 °C View Scheme

1: 52 percent / 1.5M NaOH, Bu4NHSO4 / CH2Cl2; H2O / 0.5 h / 22 °C 2: 1.) CH3ONa, 2.) 1.2M NaOH, Bu4NHSO4 / 1.) DMF, 35 deg C, 1 h, 2.) CH2Cl2, H2O, 10 min 3: 89 percent / NaOH / H2O; methanol / 0.08 h / Heating View Scheme