sodium methylate; methyl iodide in methanol T=20°C; 1 h;

chloranil in tert-butyl alcohol Heating;

mercury dichloride in ethanol Ambient temperature;

mercury dichloride in ethanol 2 h; Heating;

1: 98 percent / trimethyl orthoformate, p-toluenesulfonic acid / methanol / 3 h / 50 °C 2: H2, triphenylphosphine, rhodium acetate dimer / ethyl acetate / 20 h / 80 °C / 9000.7 Torr 3: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h 4: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 5: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating View Scheme

1: H2, triphenylphosphine, rhodium acetate dimer / ethyl acetate / 20 h / 80 °C / 9000.7 Torr 2: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h 3: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 4: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating View Scheme

1: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h 2: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 3: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating View Scheme

1: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 2: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating View Scheme

sodium hydride in tetrahydrofuran T=20°C; 2 h;

Yield given. Multistep reaction;