Reaction #833523

Reaction equation

water

6-chlorohexanol

acetic acid

pyridine

→

6-acetoxy chlorohexane

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturethey were refluxed for 2 hours
2. 2
   workup.ADDITIONwas further added
3. 3
   WashAfter neutralization the toluene layer with an aqueous saturated solution of sodium carbonate, it was washed with a small amount of water
4. 4
   Dryingfurther dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONToluene and unreacted ingredients were distilled off from the toluene layer
6. 6
   Otherto obtain concentrates
7. 7
   workup.DISTILLATIONThe concentrates were purified by distillation under a reduced pressure

Procedure

6-chlorohexanol (800 g) was added to anhydrous acetic acid (1,200 mL) cooled to 10° C. in an ice bath, and then pyridine (934 g) was dropped for 10 minutes. After the completion of dropping, they were refluxed for 2 hours. The reaction mixture was poured into water and toluene was further added and stirred. After neutralization the toluene layer with an aqueous saturated solution of sodium carbonate, it was washed with a small amount of water and further dried over anhydrous magnesium sulfate. Toluene and unreacted ingredients were distilled off from the toluene layer to obtain concentrates. The concentrates were purified by distillation under a reduced pressure to obtain 6-acetoxy chlorohexane (983 g). The boiling point was 82° C./5.3 hPa.

Source