hydrogenchloride; hydrogen; palladium on activated charcoal in ethanol T=60°C; 2 h;

1.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / tert-butyl methyl ether / 48 h / 45 °C 2.1: toluene / 6 h / Reflux 3.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / toluene / 0.17 h / 20 °C 3.2: 20 - 40 °C 4.1: hydrogenchloride; hydrogen / palladium on activated charcoal / ethanol / 2 h / 60 °C View Scheme

1.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / toluene / 0.17 h / 20 °C 1.2: 20 - 40 °C 2.1: hydrogenchloride; hydrogen / palladium on activated charcoal / ethanol / 2 h / 60 °C View Scheme

1.1: toluene / 6 h / Reflux 2.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / toluene / 0.17 h / 20 °C 2.2: 20 - 40 °C 3.1: hydrogenchloride; hydrogen / palladium on activated charcoal / ethanol / 2 h / 60 °C View Scheme

sodium hydroxide in water T=25°C; pH=11;