Reaktion #558513

ord-f2191645d2554461b1a320a48ad7f3d6

Reaktionsgleichung

CCN(CC)CC
triethylamine
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
1-menthol
O=S(Cl)Cl
thionyl chloride
CC(C)CCCCCCCCCCCCCCC(=O)O
isostearic acid
O=S(Cl)Cl
thionyl chloride
→
CC(C)CCCCCCCCCCCCCCC(=O)OC1(C)CCC(C(C)C)CC1
desired product
Ausbeute 83.1%
CC(C)CCCCCCCCCCCCCCC(=O)OC1(C)CCC(C(C)C)CC1
1-menthyl isostearate
Ausbeute 83.1%

Edukte

CCN(CC)CC
triethylamine
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
1-menthol
O=S(Cl)Cl
thionyl chloride
—
1-L
CC(C)CCCCCCCCCCCCCCC(=O)O
isostearic acid
O=S(Cl)Cl
thionyl chloride

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeequipped with a thermometer
  2. 2
    Temperaturheated at an oil bath temperature of 40° C.
  3. 3
    workup.STIRRINGstirred for 1 hour
  4. 4
    SonstigeThe reaction solution obtained
  5. 5
    workup.ADDITIONAfter dropwise addition
  6. 6
    workup.STIRRINGthe mixture was stirred at an oil bath temperature of 60° C. for 3 hours
  7. 7
    SonstigeThe reaction solution obtained
  8. 8
    Sonstigewas quenched in water
  9. 9
    Extraktionextracted with toluene
  10. 10
    WaschenThe toluene phase was washed with aqueous saturated sodium chloride solution
  11. 11
    Trocknendried over anhydrous sodium sulfate
  12. 12
    Filtrationfiltered
  13. 13
    Sonstigecondensed
  14. 14
    Sonstigein rotary evaporator
  15. 15
    Sonstigefor removal of the solvent
  16. 16
    Sonstigeto give yellow oil
  17. 17
    workup.DISTILLATIONDistillation

Vorschrift

284.5 g of isostearic acid (molecular weight: 284.49, 1.00 mol) and thionyl chloride (molecular weight: 118.97, 1.05 mol) were placed in a 1-L reaction flask equipped with a thermometer. The mixture was stirred at room temperature for 20 minutes and then, heated at an oil bath temperature of 40° C. and stirred for 1 hour. The reaction solution obtained was left under reduced pressure for removal of the dissolved gas and excess thionyl chloride. 300 ml of toluene and 156.3 g of 1-menthol (molecular weight: 156.27, 1.00 mol) were added thereto; and 121.4 g of triethylamine (molecular weight: 101.19, 1.20 mol) was added dropwise over 20 minutes. After dropwise addition, the mixture was stirred at an oil bath temperature of 60° C. for 3 hours. The reaction solution obtained was quenched in water and extracted with toluene. The toluene phase was washed with aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and condensed in rotary evaporator for removal of the solvent to give yellow oil. Distillation thereof under reduced pressure gave a desired product, isostearic acid-1-menthyl as colorless oil. Yield: 351.4 g, (molecular weight: 422.7, 831.4 mmol), purity: 99.8%, yield: 83.1%.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08632792B2uspto-grants-2014_01