sodium hydroxide; thionyl chloride 2) ether, reflux, 6 h; Yield given. Multistep reaction;

1: NaOH, benzyltriethylammonium chloride / H2O; diethyl ether / 120 h 2: 1.) aq. NaOH, 2.) SOCl2 / 2) ether, reflux, 6 h View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C 1.2: 9 h / -78 - 20 °C 1.3: 50 °C / Inert atmosphere 2.1: water; potassium hydroxide / methanol / 12 h / 25 °C 3.1: thionyl chloride / 8 h / 25 °C / neat (no solvent) View Scheme

1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0 - 25 °C / Inert atmosphere 2: water; potassium hydroxide / methanol / 12 h / 25 °C View Scheme

4-(N,N-dimethlyamino)pyridine in dichloromethane T=0 - 25°C; Inert atmosphere; optical yield given as percent de;