Phenylacetic Acid → 3-(4-Methoxyphenyl)-2-phenylprop-2-enoic acid

HRID 1935733

Reaktionsgleichung

Reaktionsgleichung von HRID 1935733
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]1([CH2:17][C:18]([OH:20])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C(OC(=O)C)(=O)C.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:18]([OH:20])=[O:19])=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 999Phenylacetic AcidHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 312444-Methoxybenzaldehyde

Produkt 1

HCID 2366983-(4-Methoxyphenyl)-2-phenylprop-2-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 4-methoxybenzaldehyde (30.0 g, 0.22 mol), phenylacetic acid (31.5 g, 0.23 mol), and triethylamine (31 ml) in acetic anhydride (75 ml) was heated at 90° C. for 5 hours. After cooling, 18 ml of water was dropped carefully during 15 min. Then, potassium carbonate (243 g) in water (1800 ml) was dropped and the solution was heated at 60° C. for 1 hour. After cooling, the solution was extracted with dichloro-methane. When the aqueous phase was acidified (pH 6-7), the product was precipitated. After stirring at 0° C., the product was filtered and dried.

Aufarbeitung

  1. temperatureAfter cooling
  2. temperaturethe solution was heated at 60° C. for 1 hour
  3. temperatureAfter cooling
  4. extractionthe solution was extracted with dichloro-methane
  5. customthe product was precipitated
  6. filtrationthe product was filtered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ca940e1761cb445f9bcf57806700419e
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06388090B2

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