1: With sulfuric acid; sodium nitrite in water T=0°C; 2: With water; hypophosphorous ether T=0 - 45°C; 1 h;

1.1: pyridine / 1,4-dioxane / 16 h / 0 - 20 °C 2.1: nitric acid; acetic acid / 15 °C 2.2: 0.5 h / |Cooling with ice 3.1: hydrogenchloride / ethanol / 2 h / |Reflux 4.1: isopentyl nitrite / tetrahydrofuran / 3.25 h / 0 °C / |Reflux View Scheme

1.1: nitric acid; acetic acid / 15 °C 1.2: 0.5 h / |Cooling with ice 2.1: hydrogenchloride / ethanol / 2 h / |Reflux 3.1: isopentyl nitrite / tetrahydrofuran / 3.25 h / 0 °C / |Reflux View Scheme

1.1: AlCl3, aluminium chloride; lithium aluminium tetrahydride / diethyl ether / 0 °C / |Reflux 2.1: silver nitrate; acetyl chloride / acetonitrile; water / 5 h / 0 - 20 °C 3.1: palladium 10 on activated carbon; hydrogen / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: pyridine / 1,4-dioxane / 16 h / 0 - 20 °C 5.1: nitric acid; acetic acid / 15 °C 5.2: 0.5 h / |Cooling with ice 6.1: hydrogenchloride / ethanol / 2 h / |Reflux 7.1: isopentyl nitrite / tetrahydrofuran / 3.25 h / 0 °C / |Reflux View Scheme

1.1: silver nitrate; acetyl chloride / acetonitrile; water / 5 h / 0 - 20 °C 2.1: palladium 10 on activated carbon; hydrogen / methanol; tetrahydrofuran / 2 h / 20 °C 3.1: pyridine / 1,4-dioxane / 16 h / 0 - 20 °C 4.1: nitric acid; acetic acid / 15 °C 4.2: 0.5 h / |Cooling with ice 5.1: hydrogenchloride / ethanol / 2 h / |Reflux 6.1: isopentyl nitrite / tetrahydrofuran / 3.25 h / 0 °C / |Reflux View Scheme

1.1: palladium 10 on activated carbon; hydrogen / methanol; tetrahydrofuran / 2 h / 20 °C 2.1: pyridine / 1,4-dioxane / 16 h / 0 - 20 °C 3.1: nitric acid; acetic acid / 15 °C 3.2: 0.5 h / |Cooling with ice 4.1: hydrogenchloride / ethanol / 2 h / |Reflux 5.1: isopentyl nitrite / tetrahydrofuran / 3.25 h / 0 °C / |Reflux View Scheme