sodium acetate; pyridinium chlorochromate in dichloromethane 2 h;

1: 91 percent / LiAlH4 2: 81 percent / propionic acid / 36 h / 138 °C 3: 95 percent / H2 / 10percent Pd/C / ethanol 4: LiAlH4 5: 76 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h View Scheme

1: 81 percent / propionic acid / 36 h / 138 °C 2: 95 percent / H2 / 10percent Pd/C / ethanol 3: LiAlH4 4: 76 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h View Scheme

1: 91 percent / LiAlH4 2: 91 percent / LiAlH4 3: 81 percent / propionic acid / 36 h / 138 °C 4: 95 percent / H2 / 10percent Pd/C / ethanol 5: LiAlH4 6: 76 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h View Scheme

1: 82.5 percent / p-CH3C6H4SO3H / benzene / Heating 2: 91 percent / LiAlH4 3: 91 percent / LiAlH4 4: 81 percent / propionic acid / 36 h / 138 °C 5: 95 percent / H2 / 10percent Pd/C / ethanol 6: LiAlH4 7: 76 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h View Scheme

1: 95 percent / H2 / 10percent Pd/C / ethanol 2: LiAlH4 3: 76 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h View Scheme

1: LiAlH4 2: 76 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h View Scheme

(i) POCl3, benzene, (ii) H2, Et3N, Pd-C, MeOH; Multistep reaction;