sulfuric acid; hydrogen; acetic acid; palladium on activated charcoal P=2844.3 Torr; Ambient temperature;

1: 71 percent / n-butylnitrite; conc. aq. HCl / methanol / 0.5 h / 40 °C 2: 42 percent / H2; H2SO4 / 10percent Pd/C / acetic acid / 7 h / 2585.81 Torr View Scheme

1: 97 percent / benzyltrimethylammonium chloride, NaOH / CH2Cl2 / 2 h / Ambient temperature 2: 95 percent / n-butyl nitrite, HCl / diethyl ether / 1 h / Ambient temperature 3: 72 percent / H2, H2SO4, AcOH / 5percent Pd/C / 2844.3 Torr / Ambient temperature View Scheme

1: 60 percent / benzyltrimethylammonium chloride, NaOH / CH2Cl2 / 4 h / Heating 2: 97 percent / benzyltrimethylammonium chloride, NaOH / CH2Cl2 / 2 h / Ambient temperature 3: 95 percent / n-butyl nitrite, HCl / diethyl ether / 1 h / Ambient temperature 4: 72 percent / H2, H2SO4, AcOH / 5percent Pd/C / 2844.3 Torr / Ambient temperature View Scheme

1: thionyl chloride, DMF / CH2Cl2 / 4 h / Heating 2: AlCl3 / CH2Cl2 / 3 h / Heating 3: 60 percent / benzyltrimethylammonium chloride, NaOH / CH2Cl2 / 4 h / Heating 4: 97 percent / benzyltrimethylammonium chloride, NaOH / CH2Cl2 / 2 h / Ambient temperature 5: 95 percent / n-butyl nitrite, HCl / diethyl ether / 1 h / Ambient temperature 6: 72 percent / H2, H2SO4, AcOH / 5percent Pd/C / 2844.3 Torr / Ambient temperature View Scheme

1: AlCl3 / CH2Cl2 / 3 h / Heating 2: 60 percent / benzyltrimethylammonium chloride, NaOH / CH2Cl2 / 4 h / Heating 3: 97 percent / benzyltrimethylammonium chloride, NaOH / CH2Cl2 / 2 h / Ambient temperature 4: 95 percent / n-butyl nitrite, HCl / diethyl ether / 1 h / Ambient temperature 5: 72 percent / H2, H2SO4, AcOH / 5percent Pd/C / 2844.3 Torr / Ambient temperature View Scheme

Yield given. Multistep reaction;