1: (S,S)-[(salen)Al]2O; t-BuOH / cyclohexane / 54 h / 20 °C 2: 86 percent / Raney nickel / toluene; methanol / 14 h / 75 °C / 33614.6 Torr 3: sodium methoxide / toluene; methanol / 1 h / 75 °C 4: lithium aluminum hydride / tetrahydrofuran; toluene / 5 h / 75 °C 5: 359 mg / aq. sodium hydroxide / tetrahydrofuran / 14 h / 20 °C 6: triethylamine / toluene / 2 h / 23 °C 7: 86 percent / sodium methoxide / toluene; methanol / 14 h / 80 - 110 °C 8: 99 percent / HCl / propan-2-ol / 5 h / 75 °C View Scheme

1: (S,S)-[(salen)Al]2O; t-BuOH / cyclohexane / 54 h / 20 °C 2: 86 percent / Raney nickel / toluene; methanol / 14 h / 75 °C / 33614.6 Torr 3: sodium methoxide / toluene; methanol / 1 h / 75 °C 4: lithium aluminum hydride / tetrahydrofuran; toluene / 5 h / 75 °C 5: 359 mg / aq. sodium hydroxide / tetrahydrofuran / 14 h / 20 °C View Scheme

1: (S,S)-[(salen)Al]2O; t-BuOH / cyclohexane / 54 h / 20 °C 2: 86 percent / Raney nickel / toluene; methanol / 14 h / 75 °C / 33614.6 Torr 3: sodium methoxide / toluene; methanol / 1 h / 75 °C 4: lithium aluminum hydride / tetrahydrofuran; toluene / 5 h / 75 °C View Scheme