Hydrochloric Acid → Ethyl 3-propoxycinnamate

HRID 1169493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169493
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:17]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O)[CH2:18][CH3:19].Cl>C1COCC1.O>[CH2:17]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:18][CH3:19]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 27604693-Propoxybenzaldehyde

Produkt 1

HCID 70025296Ethyl 3-propoxycinnamateAusbeute 104,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To ethyl diethylphosphonoacetate (24.7 g) was added THF (200 ml), and sodium hydride (60%, 4.4 g) was added at 0° C. to the resulting mixture, to which was then added dropwise a solution of 3-propoxybenzaldehyde (16.1 g) in THF (100 ml). The resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was poured into water, was neutralized with hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with anhydrous magnesium sulfate. After concentration under reduced pressure to remove the solvent, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain ethyl 3-propoxycinnamate (24.0 g) as a yellow oil.

Aufarbeitung

  1. additionwas added at 0° C. to the resulting mixture, to which
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customto remove the solvent
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-e8c985785ff64e4894904a22fa2ca67c
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627651B1

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