thionyl chloride

1: 1.) n-BuLi / 1.) THF, hexane, -60 deg C, 10 min, 2.) -65 deg C, 30 min 2: propionic acid / 145 - 180 °C 3: 10percent aq. NaOH / 6 h / Heating 4: 71 percent / thionyl chloride / 1 h / Heating View Scheme

1: propionic acid / 145 - 180 °C 2: 10percent aq. NaOH / 6 h / Heating 3: 71 percent / thionyl chloride / 1 h / Heating View Scheme

1: 10percent aq. NaOH / 6 h / Heating 2: 71 percent / thionyl chloride / 1 h / Heating View Scheme

1: 89 percent 2: CH3CH2COOH / 21 h / 145 °C 3: 10percent NaOH / H2O 4: 83 percent / thionyl chloride View Scheme