Reaktion #350328

Reaktionsgleichung

thionyl chloride

1-(1-hydroxypropyl)-2,4,6-triisopropylbenzene

thionyl chloride

1-ethyl-2',4',6'-triisopropylbenzyl alcohol

1-(1-hydroxypropyl)-2,4,6-triisopropylbenzene

→

pale yellow liquid

Ausbeute 92.0%

1-(1-Chloropropyl)-2,4,6-Triisopropylbenzene

Ausbeute 92.0%

Lösungsmittel

hexane

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 100 milliliter flask was equipped with a magnetic stirrer
2. 2
   workup.ADDITIONaddition
3. 3
   Sonstigefunnel/drying tube
4. 4
   workup.ADDITIONThe flask was filled with a solution
5. 5
   workup.ADDITIONThe addition funnel was filled with a solution
6. 6
   workup.ADDITIONDuring the addition there
7. 7
   workup.ADDITIONafter the addition the reaction mixture
8. 8
   workup.WAITwas left
9. 9
   workup.WAITstanding over night
10. 10
    Temperaturwas cooled in an ice bath
11. 11
    TemperaturAfter the reaction mixture was cooled
12. 12
    workup.STIRRINGwith stirring
13. 13
    Sonstigethe organic phase and water phase were separated
14. 14
    Waschenthe organic phase was washed with 5 portions of 20 milliliters of water
15. 15
    TrocknenThen the organic phase was dried over magnesium sulfate
16. 16
    Filtrationfiltered
17. 17
    SonstigeThe solvent was evaporated from the organic phase
18. 18
    Sonstigea rotary evaporator

Vorschrift

A 100 milliliter flask was equipped with a magnetic stirrer and a pressure equalized addition funnel/drying tube. The flask was filled with a solution containing 50 milliliters of hexane and 15 grams (0.057 mole) of 1-(1-hydroxypropyl)-2,4,6-triisopropylbenzene (1-ethyl-2',4',6'-triisopropylbenzyl alcohol). The addition funnel was filled with a solution containing 10 milliliters of hexane and 8.9 grams (0.075 mole) of thionyl chloride. The solution of the thionyl chloride was slowly added to the solution of the 1-ethyl-2',4',6'-triisopropylbenzyl alcohol over a 45 minute period while stirring the reaction mixture. During the addition there was vigorous gas evolution, and after the addition the reaction mixture was left standing over night and then was cooled in an ice bath. After the reaction mixture was cooled, about 20 milliliters of ice water was rapidly added with stirring. After warming the reaction mixture to room temperature, the organic phase and water phase were separated, and the organic phase was washed with 5 portions of 20 milliliters of water, and then with a 20 milliliter solution of saturated sodium chloride. Then the organic phase was dried over magnesium sulfate and filtered. The solvent was evaporated from the organic phase using a rotary evaporator, to give 14.0 grams (92 percent) of a pale yellow liquid of the composition 1-(1-chloropropyl)-2,4,6-triisopropylbenzene.

Quelle