1: 67.3 g / Zn / benzene / 1.5 h / Heating 2: 1.) formic acide, 2.) H2 / 2.) 5 percent Pd/C / 1.) 1 h, reflux; 2.) methanol, rt 3: 35.5 g / LiAlH4 / diethyl ether / 2 h / Heating 4: 33.4 g / PBr3 / 1.) 0 deg C up to rt., 2.) 60 deg C, 1.5 h 5: sodium ethylate / ethanol / 4 h / Heating 6: 5.8 g / aq. sodium carbonate / methanol / 2 h / Heating 7: thionyl chloride / 1 h / Heating 8: AlCl3 / CS2 / 2 h / Heating 9: Wolff-Kishner reduction (Huang-Minlon) 10: AlCl3 / CS2 / 2 h / Heating View Scheme

1: 1.) formic acide, 2.) H2 / 2.) 5 percent Pd/C / 1.) 1 h, reflux; 2.) methanol, rt 2: 35.5 g / LiAlH4 / diethyl ether / 2 h / Heating 3: 33.4 g / PBr3 / 1.) 0 deg C up to rt., 2.) 60 deg C, 1.5 h 4: sodium ethylate / ethanol / 4 h / Heating 5: 5.8 g / aq. sodium carbonate / methanol / 2 h / Heating 6: thionyl chloride / 1 h / Heating 7: AlCl3 / CS2 / 2 h / Heating 8: Wolff-Kishner reduction (Huang-Minlon) 9: AlCl3 / CS2 / 2 h / Heating View Scheme

1: AlCl3 / CS2 / 2 h / Heating 2: Wolff-Kishner reduction (Huang-Minlon) 3: AlCl3 / CS2 / 2 h / Heating View Scheme

1: 33.4 g / PBr3 / 1.) 0 deg C up to rt., 2.) 60 deg C, 1.5 h 2: sodium ethylate / ethanol / 4 h / Heating 3: 5.8 g / aq. sodium carbonate / methanol / 2 h / Heating 4: thionyl chloride / 1 h / Heating 5: AlCl3 / CS2 / 2 h / Heating 6: Wolff-Kishner reduction (Huang-Minlon) 7: AlCl3 / CS2 / 2 h / Heating View Scheme

1: sodium ethylate / ethanol / 4 h / Heating 2: 5.8 g / aq. sodium carbonate / methanol / 2 h / Heating 3: thionyl chloride / 1 h / Heating 4: AlCl3 / CS2 / 2 h / Heating 5: Wolff-Kishner reduction (Huang-Minlon) 6: AlCl3 / CS2 / 2 h / Heating View Scheme

1: 35.5 g / LiAlH4 / diethyl ether / 2 h / Heating 2: 33.4 g / PBr3 / 1.) 0 deg C up to rt., 2.) 60 deg C, 1.5 h 3: sodium ethylate / ethanol / 4 h / Heating 4: 5.8 g / aq. sodium carbonate / methanol / 2 h / Heating 5: thionyl chloride / 1 h / Heating 6: AlCl3 / CS2 / 2 h / Heating 7: Wolff-Kishner reduction (Huang-Minlon) 8: AlCl3 / CS2 / 2 h / Heating View Scheme

1: AlCl3 / CS2 / 2 h / Heating 2: Wolff-Kishner reduction (Huang-Minlon) 3: AlCl3 / CS2 / 2 h / Heating View Scheme

1: thionyl chloride / 1 h / Heating 2: AlCl3 / CS2 / 2 h / Heating 3: Wolff-Kishner reduction (Huang-Minlon) 4: AlCl3 / CS2 / 2 h / Heating View Scheme

1: 5.8 g / aq. sodium carbonate / methanol / 2 h / Heating 2: thionyl chloride / 1 h / Heating 3: AlCl3 / CS2 / 2 h / Heating 4: Wolff-Kishner reduction (Huang-Minlon) 5: AlCl3 / CS2 / 2 h / Heating View Scheme

1: Wolff-Kishner reduction (Huang-Minlon) 2: AlCl3 / CS2 / 2 h / Heating View Scheme