sodium hydroxide; sodium nitrite in hydrogenchloride; water

sodium hydroxide in ethanol; water 3.5 h; Heating;

sodium hydroxide in ethanol; water 2 h; Heating;

1: 42 percent / triethylamine / tetrahydrofuran / 1.25 h / 5 °C 2: 1.) ethyl acetate, 0.5 h, 2). 1 h 3: 88 percent / sodium hydroxide / ethanol; H2O / 3.5 h / Heating View Scheme

1: 1.) ethyl acetate, 0.5 h, 2). 1 h 2: 88 percent / sodium hydroxide / ethanol; H2O / 3.5 h / Heating View Scheme

1: 1.) ethyl acetate, 0.5 h, 2). 1 h 2: 44 percent / sodium hydroxide / ethanol; H2O / 2 h / Heating View Scheme

1: 1.) conc. hydrochloric acid, sodium nitrite, 2.) stannous chloride, hydrochloric acid / 1.) 5-10 deg C, 1 h, 2.) room temperature, 45 min 2: 42 percent / triethylamine / tetrahydrofuran / 1.25 h / 5 °C 3: 1.) ethyl acetate, 0.5 h, 2). 1 h 4: 88 percent / sodium hydroxide / ethanol; H2O / 3.5 h / Heating View Scheme

1: 69 percent / tetrahydrofuran / 1 h 2: 1.) NaOH; 2.) aq. HCl / 1.) aq. ethanol, 83 deg C, 2.5 h View Scheme

1: 75 percent 2: 1.) NaOH; 2.) aq. HCl / 1. aq. ethanol, reflux View Scheme