1: With methanol; potassium hydroxide 3 - 4 h; 2: With citric acid pH=6;

1.1: perchloric acid / ethyl acetate; water / 8 h / 18 °C / |Inert atmosphere 2.1: N-bromosuccinmide / water; N,N-dimethyl-formamide / 1.17 h / 0 - 7 °C / |Inert atmosphere 2.2: 1.58 h / 110 °C / |Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran; dimethyl-ether / 0.5 h / 0 - 10 °C / |Inert atmosphere 4.1: potassium hydroxide; water / methanol; toluene / 2 h / 40 °C / |Inert atmosphere View Scheme

1.1: N-bromosuccinmide / water; N,N-dimethyl-formamide / 1.17 h / 0 - 7 °C / |Inert atmosphere 1.2: 1.58 h / 110 °C / |Inert atmosphere 2.1: copper(l) iodide / tetrahydrofuran; dimethyl-ether / 0.5 h / 0 - 10 °C / |Inert atmosphere 3.1: potassium hydroxide; water / methanol; toluene / 2 h / 40 °C / |Inert atmosphere View Scheme

1: TsOH, CH(OEt)3 / benzene / 1.5 h / 72 °C 2: 92.1 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme

sodium acetate; toluene-4-sulfonic acid; pyridinium chlorochromate 1.) benzene, reflux, 43 h, 2.) CH2Cl2, RT, 5.5 h; Yield given. Multistep reaction;

sodium acetate; toluene-4-sulfonic acid; ethylenediamine; pyridinium chlorochromate Multistep reaction. Title compound not separated from byproducts;