1: With lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 2: With hydrogenchloride; water in tetrahydrofuran Product distribution / selectivity;

1: 72 percent / 12 M hydrochloric acid / ethanol / 24 h / Heating 2: 76 percent / lithium aluminum hydride / tetrahydrofuran / 24 h / Heating View Scheme

1: 1.) sodium pellets / 1.) toluene, room temp., 3 days, 2.) toluene, 0 deg C, 1 h then room temp., 1 day 2: 72 percent / 12 M hydrochloric acid / ethanol / 24 h / Heating 3: 76 percent / lithium aluminum hydride / tetrahydrofuran / 24 h / Heating View Scheme

Dess-Martin periodane in dichloromethane T=0°C; 2 h; Product distribution / selectivity;