1: 63 percent / H2 / Lindlar catalyst / benzene / 760 Torr 2: OsO4, N-morpholine N-oxide monohydrate / dimethylformamide; 2-methyl-propan-2-ol / 4.5 h / -20 °C 3: TsOH / acetone / 2 h / Ambient temperature 4: 82 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme

Multi-step reaction with 5 steps 1: 63 percent / H2 / Lindlar catalyst / benzene / 760 Torr2: OsO4, N-morpholine N-oxide monohydrate / dimethylformamide; 2-methyl-propan-2-ol / 4.5 h / -20 °C3: TsOH / acetone / 2 h / Ambient temperature4: 82 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature5: 58 percent / NaH / paraffin; toluene / 0.5 h / Ambient temperature  

Multi-step reaction with 5 steps 1: 63 percent / H2 / Lindlar catalyst / benzene / 760 Torr2: OsO4, N-morpholine N-oxide monohydrate / dimethylformamide; 2-methyl-propan-2-ol / 4.5 h / -20 °C3: TsOH / acetone / 2 h / Ambient temperature4: 82 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature5: 82 percent / NaH / paraffin; toluene / 0.5 h / Ambient temperature  

Multi-step reaction with 4 steps 1: OsO4, N-morpholine N-oxide monohydrate / dimethylformamide; 2-methyl-propan-2-ol / 4.5 h / -20 °C2: TsOH / acetone / 2 h / Ambient temperature3: 98 percent / LiOH / tetrahydrofuran; H2O / 7 h / Ambient temperature4: 70 percent / Me3Al / hexane / 20 h / 60 °C  

Multi-step reaction with 2 steps 1: LiOH / tetrahydrofuran; H2O / 13 h / Ambient temperature2: 70 percent / Me3Al / hexane / 20 h / 60 °C  

Multi-step reaction with 3 steps 1: 63 percent / H2 / Lindlar catalyst / benzene / 760 Torr2: OsO4, N-morpholine N-oxide monohydrate / dimethylformamide; 2-methyl-propan-2-ol / 4.5 h / -20 °C3: TsOH / acetone / 2 h / Ambient temperature