1: 45 percent / sodium azide, hexadecyltributylphosphonium bromide / benzene; H2O / 4 h / 35 °C 2: 18 percent / benzene / 4 h / Heating View Scheme

hydrogenchloride; sodium acetate; sodium nitrite 1.) water; 2.) ethanol-water, 0 deg C, 3 h, overnight; Multistep reaction;

sodium ethanolate in ethanol 18 h; Ambient temperature;