Pyridine → 1-Chloro-5-ethoxyheptane

The starting material prepared in Example 37, 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 a clear light yellow oil. The crude product is fractionally distilled under reduced pressure leaving a clear, colorless oil (162 g, 1.13 moles), BP 96° C./9.5 cm Hg.

1. temperatureafter which time the reaction is heated in a 70° C. water bath for 2 additional hours
2. customthe organic layer separated
3. extractionThe aqueous layer is extracted with hexane (3×400 ml)
4. washThe organic phase is then washed with a 10% sodium hydroxide solution (1000 ml)
5. dry with materialthe residue dried over anhydrous magnesium sulfate
6. customThe remaining solvent is removed
7. customleaving a clear light yellow oil
8. distillationThe crude product is fractionally distilled under reduced pressure

ORD record

ord-ef755968333d418193b548fbcc4d892b

Source dataset

uspto-grants-1987_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04689345