potassium hydroxide in methanol; ethanol; toluene T=130°C; 1 h;

1: (i) N,N-diethyl-4-nitroso-aniline, (ii) aq. HCl 2: <PhCH2NMe3>OH / methanol View Scheme

1: (i), (ii) aq. HCl 2: (i) N,N-diethyl-4-nitroso-aniline, (ii) aq. HCl 3: <PhCH2NMe3>OH / methanol View Scheme

1: periodic acid; acetic acid / 20 h / 55 °C 2: potassium hydroxide / ethanol; toluene; methanol / 1 h / 130 °C View Scheme

1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 20 h / 20 °C / |Inert atmosphere 2: periodic acid; acetic acid / 20 h / 55 °C 3: potassium hydroxide / ethanol; toluene; methanol / 1 h / 130 °C View Scheme

in benzene

1: benzene 2: HBr / benzene View Scheme