Réaction #66039

Équation de réaction

methanesulfonyl chloride

behenyl alcohol

triethylamine

→

white crystal

1-docosanyl methanesulfonate

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGfurther stirred for 30 minutes
2. 2
   workup.ADDITIONthe resulting mixture was ultrasonically dispersed for 15 minutes
3. 3
   workup.STIRRINGfurther stirred at room temperature for 4 hours
4. 4
   FiltrationThe dispersion was filtered under reduced pressure
5. 5
   Lavagea crystal was washed with 2 L of water
6. 6
   workup.STIRRINGThe resulting white crystal was stirred in 1.5 L of acetonitrile for one hour
7. 7
   Filtrationfiltered under reduced pressure
8. 8
   Lavagewashed with 0.5 L of acetonitrile
9. 9
   AutreThe resulting crystal was dried under reduced pressure

Mode opératoire

247.4 g of behenyl alcohol (1-docosanol) was dissolved in 640 mL of tetrahydrofuran, 116.1 mL of methanesulfonyl chloride was gradually added, and 64.7 mL of triethylamine was then added dropwise under ice cooling over 30 minutes. After stirring for one hour, the mixture was heated at 40° C. and further stirred for 30 minutes. The reaction mixture was poured into 3.5 L of ice water, and the resulting mixture was ultrasonically dispersed for 15 minutes and further stirred at room temperature for 4 hours. The dispersion was filtered under reduced pressure, and a crystal was washed with 2 L of water. The resulting white crystal was stirred in 1.5 L of acetonitrile for one hour, filtered under reduced pressure and then washed with 0.5 L of acetonitrile. The resulting crystal was dried under reduced pressure to obtain 303.4 g of a white crystal.

Source