Pyridine → 1-Chloro-5-ethoxyheptane

Participants

Reaction Steps

5-Ethoxyheptanol (238 g, 1.49 moles) is diluted in pyridine (128 g, 1.62 moles). The solution is stirred at room temperature and thionyl chloride (388 g, 3.22 moles) is added dropwise over 2 hours, after which time the reaction is heated in a 70° C. water bath for 2 additional hours. Water (700 ml) is added to the reaction and the organic layer separated. The aqueous layer is extracted with hexane (3×400 ml) and the extracts combined with the organic phase. The organic phase is then washed with a 10% sodium hydroxide solution (1000 ml). The solvent volume is reduced under vacuum and the residue dried over anhydrous magnesium sulfate. The remaining solvent is removed leaving 1-chloro-5-ethoxyheptane as a clear light yellow oil. The crude product is fractionally distilled under reduced pressure leaving 1-chloro-5-ethoxyheptane as a clear, colorless oil (162 g, 1.13 moles), BP 96° C./9.5 cm Hg.

Provenance & Evidence