Morpholine → Ethyl 2,6-dimethyl-3-(propan-2-yl)benzoate

HRID 1153844

Reaktionsgleichung

Reaktionsgleichung von HRID 1153844
N1CCOC[CH2:2]1.[CH:7](=O)[CH2:8][CH:9](C)C.S([O-])([O-])(=O)=O.[Mg+2].[CH3:19][C:20]1[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([CH3:31])O[C:22](=O)[CH:21]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:19][C:20]1[C:21]([CH:8]([CH3:9])[CH3:7])=[CH:22][CH:2]=[C:24]([CH3:31])[C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 115523-MethylbutanalHCID 24083Sulfuric acid magnesium salt (1:1)HCID 76918ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate

Produkt 1

HCID 13126300Ethyl 2,6-dimethyl-3-(propan-2-yl)benzoateAusbeute 8,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Morpholine (13.34 g), isovaleraldehyde (13.18 g), p-toluene sulfonic acid (0.2 g), and toluene (300 ml) were combined and heated at reflux using a Soxhlet extractor containing magnesium sulfate to remove any water produced. After three hours the Soxhlet extractor was replaced with a condenser, and ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (30 g) was added. The reaction mixture was heated under reflux for approximately 64 hours. The solvent was evaporated, and the resultant oil was distilled at atmospheric pressure to give 11.1 g of crude product which was chromatographed to yield ethyl 2,6-dimethyl-3-(1-methylethyl)benzoate (2.8 g).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux
  3. customto remove any water
  4. customproduced
  5. temperatureThe reaction mixture was heated
  6. temperatureunder reflux for approximately 64 hours
  7. customThe solvent was evaporated
  8. distillationthe resultant oil was distilled at atmospheric pressure
  9. customto give 11.1 g of crude product which
  10. customwas chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-22f9ba656ea947e6983cb4244d259aeb
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04486588

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