sodium hydride in N,N-dimethyl-formamide 1.5 h; Ambient temperature;

1: methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate With potassium carbonate in dimethyl sulfoxide T=20°C; 0.5 h; 2: methyl iodide in dimethyl sulfoxide 44 h;

1: methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate With sodium hydroxide in ethanol T=0 - 20°C; Inert atmosphere; 2: dimethyl sulfate in ethanol 5 h; Inert atmosphereReflux;

1: 85 percent / K2CO3 / acetone / Ambient temperature 2: 94 percent / 12 h / 165 °C 3: 95 percent / K2CO3 / acetone / Heating 4: 87 percent / Na-Hg / methanol; ethyl acetate / -20 °C 5: 90 percent / LiBr / tetrahydrofuran / 12 h 6: 73 percent / KI, K2CO3 / acetone / 48 h / 60 °C 7: 85 percent / H2O2, H2SO4 / CH2Cl2 / 0.17 h 8: 97 percent / imidazole, DMAP / CH2Cl2 9: 95 percent / quinoline / 10percent Pd/CaCO3 / ethyl acetate 10: 95 percent / toluene / 2 h / 100 °C 11: 1.) L-Selectride, 2.) DMAP / 1.) THF 12: 65 percent / DBU / 1 h / Ambient temperature 13: 50 percent / 4 h / 200 °C View Scheme

1: potassium carbonate / N,N-dimethyl-formamide 2: nitric acid 3: palladium 10 on activated carbon; hydrogen; acetic acid / ethanol View Scheme

1: 95 percent / 1,3-dibromo-5,5-dimethylhydantoin / CHCl3 / 10 h / 20 °C 2: 95 percent / potassium carbonate / dimethylformamide / 12 h / 70 °C View Scheme