p-Toluenesulfonic acid → Methyl Caffeate

HRID 416031

Reaktionsgleichung

Reaktionsgleichung von HRID 416031
[C:1]([OH:13])(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.[CH3:14]C1C=CC(S(O)(=O)=O)=CC=1.COC(OC)(C)C>CO>[C:1]([O:13][CH3:14])(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 689043Caffeic Acid

Produkt 1

HCID 689075Methyl CaffeateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Put a 10 g caffeic acid (1) in a reaction bottle, and add 1 g TsOH and 3 ml 2,2-dimethoxypropane and 10 ml methanol thereinto, followed by refluxing for 6 hours. After the refluxation, remove the solvent and pour the resultant solution into 100 ml water, followed by being extracted by the ethyl acetate for three times, neutralizing with 3% NaHCO3, and finally performing a column chromatography. Therefore, the product, methyl caffeate (the compound 2) is obtained with 98% yield.

Aufarbeitung

  1. temperatureby refluxing for 6 hours
  2. customAfter the refluxation, remove the solvent
  3. additionpour the resultant solution into 100 ml water
  4. extractionby being extracted by the ethyl acetate for three times

Quellen und Nachweise

ORD-Eintrag
ord-8061bc708c5948a997c7e01eb3eddcbe
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088818B2

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