1.1: 89 percent / isoamyl nitrite; lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C 2.1: 84 percent / H2; HCl / Pd/C / ethanol; H2O / 24 h / 50 °C / 12928.7 Torr 3.1: (-)-D-mandelic acid; 5-nitrosalicylaldehyde / isopropyl acetate; propan-2-ol / 45 °C 3.2: 61.4 percent / HCl / ethyl acetate; H2O / 4 h / 50 °C View Scheme

1: 89 percent / isoamyl nitrite; lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C 2: 84 percent / H2; HCl / Pd/C / ethanol; H2O / 24 h / 50 °C / 12928.7 Torr View Scheme

aluminium trichloride T=140°C; 15 h;

sodium hydride in tetrahydrofuran; N,N-dimethyl-formamide T=50°C; 2.5 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 67.1 percent / sodium bicarbonate / H2O; various solvent(s) / 1 h / 10 °C 2: 65.2 percent / AlCl3 / 1,2-dichloro-benzene / 2 h / 165 °C View Scheme

trifluoroacetic anhydride T=0°C;

1: tetrahydrofuran / 5 h 2: 67.1 percent / sodium bicarbonate / H2O; various solvent(s) / 1 h / 10 °C 3: 65.2 percent / AlCl3 / 1,2-dichloro-benzene / 2 h / 165 °C View Scheme