Thionyl Chloride → HCID 21316018, compound

HRID 263146Notes

Reaction equation

HRID 263146 reaction equation
O[CH:2]([C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([CH:14]([CH3:16])[CH3:15])=[CH:7][C:6]=1[CH:17]([CH3:19])[CH3:18])[CH2:3][CH3:4].S(Cl)([Cl:22])=O>CCCCCC>[Cl:22][CH:2]([C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([CH:14]([CH3:16])[CH3:15])=[CH:7][C:6]=1[CH:17]([CH3:19])[CH3:18])[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 21316026HCID 21316026, compound2×

Product 1

HCID 21316018HCID 21316018, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

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.

Workup

  1. customA 100 milliliter flask was equipped with a magnetic stirrer
  2. additionaddition
  3. customfunnel/drying tube
  4. additionThe flask was filled with a solution
  5. additionThe addition funnel was filled with a solution
  6. additionDuring the addition there
  7. additionafter the addition the reaction mixture
  8. waitwas left
  9. waitstanding over night
  10. temperaturewas cooled in an ice bath
  11. temperatureAfter the reaction mixture was cooled
  12. stirringwith stirring
  13. customthe organic phase and water phase were separated
  14. washthe organic phase was washed with 5 portions of 20 milliliters of water
  15. dry with materialThen the organic phase was dried over magnesium sulfate
  16. filtrationfiltered
  17. customThe solvent was evaporated from the organic phase
  18. customa rotary evaporator

Sources & evidence

ORD record
ord-06378cf9e1894fcba9dd52fcc8e89d20
Source dataset
uspto-grants-1979_05
Patent number
US04156602

Reaction notes

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