Sulfuric Acid → Methyl 3-(4-chlorophenyl)-2-propenoate

HRID 1090577

Reaktionsgleichung

Reaktionsgleichung von HRID 1090577
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:18](=O)(O)[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:18])=[O:9])=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 153712-Propenoic acid, 3-(4-chlorophenyl)-HCID 516892Sodium Bicarbonate

Produkt 1

HCID 98955Methyl 3-(4-chlorophenyl)-2-propenoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

25.9 g of p-chlorocinnamic acid was dissolved in 250 ml of methanol, to the solution was added 1.5 ml of concentrated sulfuric acid, and the mixture was refluxed for 2 hours. The reaction mixture was poured on ice, and the mixture was alkalized with sodium bicarbonate and extracted twice with 1000 ml of chloroform. The extract was washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate and evaporated to remove the solvent under a reduced pressure, and resulting residue was applied to a silica gel column and eluted with hexane/ethyl acetate (10:1), to obtain 26.5 g of the methyl p-chlorocinnamate.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 hours
  2. additionThe reaction mixture was poured on ice
  3. extractionextracted twice with 1000 ml of chloroform
  4. washThe extract was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto remove the solvent under a reduced pressure
  8. customresulting residue
  9. washeluted with hexane/ethyl acetate (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-86dd9c7be2b94bc1a3dae1b8822b885e
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081246

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