Triethylamine → 1-Menthyl isostearate

HRID 471331

Reaktionsgleichung

Reaktionsgleichung von HRID 471331
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17].S(Cl)(Cl)=O.[CH3:25][C@H:26]1[CH2:31][C@@H:30](O)[C@H:29]([CH:33]([CH3:35])[CH3:34])[CH2:28][CH2:27]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([O:20][C:26]1([CH3:25])[CH2:31][CH2:30][CH:29]([CH:33]([CH3:35])[CH3:34])[CH2:28][CH2:27]1)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 16666(-)-MentholHCID 2185916-Methylheptadecanoic AcidHCID 24386Thionyl Chloride2×

Produkt 1

HCID 1317311401-Menthyl isostearateAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

  1. customequipped with a thermometer
  2. temperatureheated at an oil bath temperature of 40° C.
  3. stirringstirred for 1 hour
  4. customThe reaction solution obtained
  5. additionAfter dropwise addition
  6. stirringthe mixture was stirred at an oil bath temperature of 60° C. for 3 hours
  7. customThe reaction solution obtained
  8. customwas quenched in water
  9. extractionextracted with toluene
  10. washThe toluene phase was washed with aqueous saturated sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customcondensed
  14. customin rotary evaporator
  15. customfor removal of the solvent
  16. customto give yellow oil
  17. distillationDistillation

Quellen und Nachweise

ORD-Eintrag
ord-f2191645d2554461b1a320a48ad7f3d6
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08632792B2

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