aluminium trichloride in dichloromethane T=-5 - 10°C; 19 h;

1: γ-chlorobutyryl chloride With AlCl3, aluminium chloride in dichloromethane T=0 - 5°C; Inert atmosphere; 2: (2-acetoxy-1,1-dimethylethyl)benzene in dichloromethane T=0°C; Inert atmosphere;

1: γ-chlorobutyraldehyde With AlCl3, aluminium chloride in dichloromethane T=-5 - 0°C; 2.33333 h; 2: (2-acetoxy-1,1-dimethylethyl)benzene in dichloromethane T=0°C; 5 h;

1: 99 percent / LiAlH4 / diethyl ether 2: 97 percent / Et3N; 4-pyrrolidinopyridine / 0.33 h / 20 °C 3: 63.5 percent / AlCl3 / CS2 / 1.5 h / 0 - 5 °C View Scheme

1: 97 percent / Et3N; 4-pyrrolidinopyridine / 0.33 h / 20 °C 2: 63.5 percent / AlCl3 / CS2 / 1.5 h / 0 - 5 °C View Scheme

1: NaOH; H2O / methanol / 12 h / 80 °C 2: 99 percent / LiAlH4 / diethyl ether 3: 97 percent / Et3N; 4-pyrrolidinopyridine / 0.33 h / 20 °C 4: 63.5 percent / AlCl3 / CS2 / 1.5 h / 0 - 5 °C View Scheme

1.1: sulfuric acid / 20 °C 2.1: 1-methyl-pyrrolidin-2-one / 160 - 165 °C 3.1: AlCl3, aluminium chloride / dichloromethane / 0 - 5 °C / Inert atmosphere 3.2: 0 °C / Inert atmosphere View Scheme

1.1: 1-methyl-pyrrolidin-2-one / 160 - 165 °C 2.1: AlCl3, aluminium chloride / dichloromethane / 0 - 5 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere View Scheme

1.1: AlCl3, aluminium chloride; Propylene glycol / methyl acetate / 0 - 5 °C 2.1: AlCl3, aluminium chloride / dichloromethane / 2.33 h / -5 - 0 °C 2.2: 5 h / 0 °C View Scheme

1: 68 percent / p-TsOH*H2O / benzene / 24 h / Heating 2: 99 percent / NaOH; MeOH / 0.5 h / 20 °C 3: 89 percent / Jones reagent / acetone / 0 °C 4: 92 percent / diethyl ether / 0 °C 5: 89 percent / HCl; H2O / tetrahydrofuran / 15 h / 20 °C 6: 95 percent / NaBH4 / methanol; tetrahydrofuran / 0.5 h / 0 °C 7: 44 percent / K2CO3; KI / dimethylformamide; toluene / 7 h / Heating 8: 67.6 percent / NaOH; MeOH / 2 h / Heating View Scheme