Neutral lead acetate; acetic acid T=80°C; Yield given. Yields of byproduct given;

1: p-toluenesulfonic acid / methanol / 5.5 h / Heating 2: 1.) 1.6 M butyllithium / 1.) hexane, THF, a.) -15 to -17 deg C, 30 min, b.) RT, 1 h, 2.) RT, 10 h 3: p-toluenesulfonic acid / 5 h / 110 - 130 °C / 170 - 200 Torr 4: hydrochloric acid / H2O / 25 °C / var. -log<H+> values of the solution View Scheme

1: 1.) 1.6 M butyllithium / 1.) hexane, THF, a.) -15 to -17 deg C, 30 min, b.) RT, 1 h, 2.) RT, 10 h 2: p-toluenesulfonic acid / 5 h / 110 - 130 °C / 170 - 200 Torr 3: hydrochloric acid / H2O / 25 °C / var. -log<H+> values of the solution View Scheme

1: p-toluenesulfonic acid / 5 h / 110 - 130 °C / 170 - 200 Torr 2: hydrochloric acid / H2O / 25 °C / var. -log<H+> values of the solution View Scheme

hydrogenchloride in methanol 0.333333 h; Ambient temperature;

hydrogenchloride in methanol 0.333333 h; Ambient temperature;

hydrogenchloride in methanol 0.333333 h; Ambient temperature;

sulfuric acid; water; mercury(II) oxide

1: phenyl lithium; diethyl ether; 5-chloro-pent-1-yne 2: mercury (II)-oxide; sulfuric acid; water View Scheme