1: With Jone's reagent in acetone T=0°C; 0.5 h; 2: With hydrogenchloride in chloroform; water Cooling with ice;

1: With lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 0.333333 h; Inert atmosphere; 2: With hydrogenchloride in water T=20°C;

hydrogenchloride Ambient temperature;

hydrogenchloride; toluene-4-sulfonic acid in xylene 7.5 h; Heating;

1: Pd-C 2: DDQ, aq. NaOH / benzene View Scheme

1: 88.8 percent / 1) NaBH4; 2) 10 percent aq. NaOH / 0.5 h / Ambient temperature 2: 79.7 percent / 1) Jones reagent; 2) 10 percent aq. NaOH, aq. HCl / acetone / 0.5 h / 0 °C View Scheme

1.1: dihydrogen peroxide; potassium hydroxide / methanol; water / 0.5 h / 65 °C / Inert atmosphere 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere 3.1: 0.5 h / Inert atmosphere 4.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere 5.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere 7.2: 20 °C View Scheme

1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere 2.1: 0.5 h / Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere 4.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere 6.2: 20 °C View Scheme

1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere 2.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere 4.2: 20 °C View Scheme

1.1: 0.5 h / Inert atmosphere 2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere 3.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere 4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere 5.2: 20 °C View Scheme