sodium hydroxide in ethanol 0.25 h; 90 deg C bath;

1: triethylamine / CHCl3 2: POCl3 / 0.5 h / 100 - 110 °C 3: 80.8 percent / 2N NaOH / ethanol / 0.25 h / 90 deg C bath View Scheme

1: SOCl2 / 1 h / Heating 2: NaBH4, 2N HCl / 1,2-dimethoxy-ethane / ice cooling 30 min, reflux 30 min 3: SOCl2 / 0.5 h / Ambient temperature 4: dimethylsulfoxide / 1.5 h 5: 2N NaOH / ethanol / 3 h / Heating View Scheme

1: SOCl2 / 1 h / Heating 2: NaBH4, 2N HCl / 1,2-dimethoxy-ethane / ice cooling 30 min, reflux 30 min View Scheme