1: With (R)-(-)-α-hydroxybenzeneacetic acid in isopropanol acetate; isopropyl alcohol T=45°C; 3 h; 2: With 2-hydroxy-5-nitro-benzaldehyde in isopropanol acetate; isopropyl alcohol 13 h; 3: With hydrogenchloride; water in ethyl acetate T=50°C; 3 h;

1.1: 65.2 percent / AlCl3 / 1,2-dichloro-benzene / 2 h / 165 °C 2.1: 89 percent / isoamyl nitrite; lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C 3.1: 84 percent / H2; HCl / Pd/C / ethanol; H2O / 24 h / 50 °C / 12928.7 Torr 4.1: (-)-D-mandelic acid; 5-nitrosalicylaldehyde / isopropyl acetate; propan-2-ol / 45 °C 4.2: 61.4 percent / HCl / ethyl acetate; H2O / 4 h / 50 °C View Scheme

1.1: tetrahydrofuran / 5 h 2.1: 67.1 percent / sodium bicarbonate / H2O; various solvent(s) / 1 h / 10 °C 3.1: 65.2 percent / AlCl3 / 1,2-dichloro-benzene / 2 h / 165 °C 4.1: 89 percent / isoamyl nitrite; lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C 5.1: 84 percent / H2; HCl / Pd/C / ethanol; H2O / 24 h / 50 °C / 12928.7 Torr 6.1: (-)-D-mandelic acid; 5-nitrosalicylaldehyde / isopropyl acetate; propan-2-ol / 45 °C 6.2: 61.4 percent / HCl / ethyl acetate; H2O / 4 h / 50 °C View Scheme

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

1.1: 67.1 percent / sodium bicarbonate / H2O; various solvent(s) / 1 h / 10 °C 2.1: 65.2 percent / AlCl3 / 1,2-dichloro-benzene / 2 h / 165 °C 3.1: 89 percent / isoamyl nitrite; lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C 4.1: 84 percent / H2; HCl / Pd/C / ethanol; H2O / 24 h / 50 °C / 12928.7 Torr 5.1: (-)-D-mandelic acid; 5-nitrosalicylaldehyde / isopropyl acetate; propan-2-ol / 45 °C 5.2: 61.4 percent / HCl / ethyl acetate; H2O / 4 h / 50 °C View Scheme