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

HRID 354544

Reaktionsgleichung

Reaktionsgleichung von HRID 354544
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-toluenesulfonic acid (0.2 g), and toluene (300 ml) were combined and heated at reflux using a Soxhlet extractor with 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 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
  9. customto give 11.1 g of crude product which
  10. customwas chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-3deaa738e08b489ea56184426ebd4810
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04375476

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