Thionyl Chloride → 3-(8-Chlorooctyl)pyridine

HRID 1249581Notes

Reaction equation

HRID 1249581 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]O)[CH:2]=1.S(Cl)([Cl:18])=O>C(Cl)Cl>[Cl:18][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 118306233-Pyridineoctanol

Product 1

HCID 137545053-(8-Chlorooctyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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°

Sources & evidence

ORD record
ord-91dfb436a934443faa442a8e0dec9199
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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