1: 1.) sodium hydride / 1.) dimethoxyethane, 30 min, room temperature 2.) reflux, 5 h, dimethoxy ethane 2: 96 percent / hydrogen / 5percent palladium on charcoal / ethanol / 6 h / 760 Torr 3: 85 percent / lithium aluminium hydride / tetrahydrofuran / 0.5 h 4: 57 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / other reagent 5: 1.) n-butyl-lithium, TMEDA 2.) n-butyl-lithium / 1.) hexane, THF, 0 deg C, 15 min 2.) 30 min, hexane, THF 6: 23 percent / toluene-p-sulphonic acid / benzene / 0.02 h View Scheme

1: 96 percent / hydrogen / 5percent palladium on charcoal / ethanol / 6 h / 760 Torr 2: 85 percent / lithium aluminium hydride / tetrahydrofuran / 0.5 h 3: 57 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / other reagent 4: 1.) n-butyl-lithium, TMEDA 2.) n-butyl-lithium / 1.) hexane, THF, 0 deg C, 15 min 2.) 30 min, hexane, THF 5: 23 percent / toluene-p-sulphonic acid / benzene / 0.02 h View Scheme

toluene-4-sulfonic acid in benzene 0.0166667 h;

1: 1.) n-butyl-lithium, TMEDA 2.) n-butyl-lithium / 1.) hexane, THF, 0 deg C, 15 min 2.) 30 min, hexane, THF 2: 23 percent / toluene-p-sulphonic acid / benzene / 0.02 h View Scheme

1: 57 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / other reagent 2: 1.) n-butyl-lithium, TMEDA 2.) n-butyl-lithium / 1.) hexane, THF, 0 deg C, 15 min 2.) 30 min, hexane, THF 3: 23 percent / toluene-p-sulphonic acid / benzene / 0.02 h View Scheme

1: 85 percent / lithium aluminium hydride / tetrahydrofuran / 0.5 h 2: 57 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / other reagent 3: 1.) n-butyl-lithium, TMEDA 2.) n-butyl-lithium / 1.) hexane, THF, 0 deg C, 15 min 2.) 30 min, hexane, THF 4: 23 percent / toluene-p-sulphonic acid / benzene / 0.02 h View Scheme

1: 96 percent / H2 / Pd, C 2: 85 percent / LiAlH4 3: 57 percent / PCC 4: 1.) BuLi 5: 28 percent / TsOH View Scheme

toluene-4-sulfonic acid

1: 64 percent / MCPBA / ethanol / 0.5 h / 0 °C 2: 77 percent / Heating View Scheme