sodium hydroxide in water 5 h; Reflux;

1: dichloromethane / 16.5 h / 0 - 20 °C 2: magnesium sulphate heptahydrate; potassium permanganate / water / 3 h / |Reflux 3: sodium hydroxide / water / 5 h / |Reflux View Scheme

1: magnesium sulphate heptahydrate; potassium permanganate / water / 3 h / |Reflux 2: sodium hydroxide / water / 5 h / |Reflux View Scheme

1: dichloromethane / 20.5 h / 0 - 20 °C 2: bromine; acetic acid / 4 h / 0 - 20 °C 3: magnesium sulphate heptahydrate; potassium permanganate / water / 3 h / |Reflux 4: sodium hydroxide / water / 5 h / |Reflux View Scheme

1: bromine; acetic acid / 4 h / 0 - 20 °C 2: magnesium sulphate heptahydrate; potassium permanganate / water / 3 h / |Reflux 3: sodium hydroxide / water / 5 h / |Reflux View Scheme

1.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / |Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / |Inert atmosphere; |Cooling with ice 2.2: |Inert atmosphere 3.1: sodium hydride / 6.5 h / 20 °C / |Inert atmosphere 4.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 5.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 6.1: tetrakis(triphenylphosphine) palladium(0); morpholine / tetrahydrofuran / 20 °C 7.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 8.1: sodium methylate / methanol / 20 °C View Scheme

1.1: pyridine / dichloromethane; acetonitrile / 3 h / 50 °C 2.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.75 h / |Cooling with ice 2.2: 5 h / 20 °C 3.1: sodium hydride / paraffin oil / 6.5 h / 20 °C 4.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 5.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C 6.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere; |Darkness 6.2: 0.3 h / 90 - 100 °C / |Inert atmosphere; |Darkness 7.1: sodium methylate; methanol / 1 h / 20 °C View Scheme