1: H2 / 10percent Pd/C / benzene; ethanol / 760 Torr / Ambient temperature 2: 1.) 33percent NaNO2/H2O, conc. HCl, ethyl acrylate, 2.) Cu2O / 1.) acetone, ice cooling, 2.) 40 deg C, 2 h 3: 29.1 g / 25percent NaOH/H2O / methanol 5: 360 mg / 20percent HCl / 4 h / Ambient temperature 6: 220 mg / BBr3 / CH2Cl2 / 0.33 h / Ambient temperature 7: 200 mg / NaN3 / dimethylsulfoxide; H2O / 3 h / 90 °C 8: 1.) H2, 2.) HCl/Et2O / 1.) 10percent Pd/C / 1.) ethanol, 1 atm, r.t. View Scheme

1: 1.) 33percent NaNO2/H2O, conc. HCl, ethyl acrylate, 2.) Cu2O / 1.) acetone, ice cooling, 2.) 40 deg C, 2 h 2: 29.1 g / 25percent NaOH/H2O / methanol 4: 360 mg / 20percent HCl / 4 h / Ambient temperature 5: 220 mg / BBr3 / CH2Cl2 / 0.33 h / Ambient temperature 6: 200 mg / NaN3 / dimethylsulfoxide; H2O / 3 h / 90 °C 7: 1.) H2, 2.) HCl/Et2O / 1.) 10percent Pd/C / 1.) ethanol, 1 atm, r.t. View Scheme

2: 360 mg / 20percent HCl / 4 h / Ambient temperature 3: 220 mg / BBr3 / CH2Cl2 / 0.33 h / Ambient temperature 4: 200 mg / NaN3 / dimethylsulfoxide; H2O / 3 h / 90 °C 5: 1.) H2, 2.) HCl/Et2O / 1.) 10percent Pd/C / 1.) ethanol, 1 atm, r.t. View Scheme

1: 29.1 g / 25percent NaOH/H2O / methanol 3: 360 mg / 20percent HCl / 4 h / Ambient temperature 4: 220 mg / BBr3 / CH2Cl2 / 0.33 h / Ambient temperature 5: 200 mg / NaN3 / dimethylsulfoxide; H2O / 3 h / 90 °C 6: 1.) H2, 2.) HCl/Et2O / 1.) 10percent Pd/C / 1.) ethanol, 1 atm, r.t. View Scheme

1: 72 percent / NaH / dimethylsulfoxide / 3 h / 60 °C 2: H2 / 10percent Pd/C / benzene; ethanol / 760 Torr / Ambient temperature 3: 1.) 33percent NaNO2/H2O, conc. HCl, ethyl acrylate, 2.) Cu2O / 1.) acetone, ice cooling, 2.) 40 deg C, 2 h 4: 29.1 g / 25percent NaOH/H2O / methanol 6: 360 mg / 20percent HCl / 4 h / Ambient temperature 7: 220 mg / BBr3 / CH2Cl2 / 0.33 h / Ambient temperature 8: 200 mg / NaN3 / dimethylsulfoxide; H2O / 3 h / 90 °C 9: 1.) H2, 2.) HCl/Et2O / 1.) 10percent Pd/C / 1.) ethanol, 1 atm, r.t. View Scheme

1: 200 mg / NaN3 / dimethylsulfoxide; H2O / 3 h / 90 °C 2: 1.) H2, 2.) HCl/Et2O / 1.) 10percent Pd/C / 1.) ethanol, 1 atm, r.t. View Scheme

hydrogenchloride; diethyl ether; hydrogen; palladium on activated charcoal 1.) ethanol, 1 atm, r.t.; Yield given. Multistep reaction;