potassium hydroxide in methanol

1: With lithium aluminium tetrahydride in tetrahydrofuran T=0 - 20°C; 3.5 h; Inert atmosphere; 2: With sodium hydroxide in tetrahydrofuran; water

1: KOH / methanol 2: SOCl2 3: 32.5 percent / AlCl3 / CH2Cl2 / 1.5 h / -30 °C 4: 1.) p-toluene-sulfonic acid monohydrate; 2.) hydrogen / 2.) PtO2 / 1.) benzene, reflux, 2.5 h; 2.) ethanol, 2.5 atm. 5: hydrogen / 10 percent Pd-on-charcoal / ethanol / 4 h / 1520 Torr View Scheme