反应详情

A 3-L flask equipped with a mechanical stirrer, thermometer, and addition funnel was charged with 145.8 g of 3-pyridineoctanol and 1.0 L of methylene chloride. The solution was cooled in an ice bath and 72 mL of thionyl chloride, diluted to 500 mL with methylene chloride, was added dropwise over 15 minutes. The cooling bath was removed and the mixture was heated at a gentle reflux for 1.0 hour. The mixture was again cooled in an ice bath and treated with 750 mL of 3N sodium hydroxide. The separated aqueous phase was extracted with 2×250 mL=500 mL of methylene chloride. The combined organic solutions were dried over sodium sulfate to which was added 10 g of Norite A charcoal. The mixture was filtered through Celite and the solvent was stripped on a rotary evaporator at 45°. The residue was co-stripped with 100 mL of toluene to give 191.3 g (overweight) of the desired 3-(8-chlorooctyl)pyridine as a brown oil which was used without further purification.

1. customA 3-L flask equipped with a mechanical stirrer
2. additionthermometer, and addition funnel
3. temperatureThe solution was cooled in an ice bath
4. additionwas added dropwise over 15 minutes
5. customThe cooling bath was removed
6. temperaturethe mixture was heated at
7. temperaturea gentle reflux for 1.0 hour
8. temperatureThe mixture was again cooled in an ice bath
9. additiontreated with 750 mL of 3N sodium hydroxide
10. extractionThe separated aqueous phase was extracted with 2×250 mL=500 mL of methylene chloride
11. dry with materialThe combined organic solutions were dried over sodium sulfate to which
12. additionwas added 10 g of Norite A charcoal
13. filtrationThe mixture was filtered through Celite
14. customthe solvent was stripped on a rotary evaporator at 45°