N-benzyl-trimethylammonium hydroxide in 1,4-dioxane T=0 - 20°C;

1: 82 percent / p-toluene sulfonic acid / benzene / 3 h / Heating 2: LiAlH4 / tetrahydrofuran / 3 h / Heating 3: 10percent aq. HCl / 1 h / Ambient temperature 4: 10percent aq. NaOH / 1 h / Ambient temperature; pH = 9 5: 96 percent / hydrogen / 5percent Pd/C / aq. ethanol / 3 h / 2327.2 Torr View Scheme

1: 82 percent / p-toluene sulfonic acid / benzene / 3 h / Heating 2: LiAlH4 / tetrahydrofuran / 3 h / Heating 3: 10percent aq. HCl / 1 h / Ambient temperature 4: 10percent aq. NaOH / 1 h / Ambient temperature; pH = 9 View Scheme