Acetic Acid → 4-Ethylresorcinol

HRID 1072949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072949
C(O)C.[CH3:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:14])=[CH:11][C:12]=1[OH:13])=O.C(O)(=O)C>[Ni].O>[CH2:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:14])=[CH:11][C:12]=1[OH:13])[CH3:4]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 702Ethanol2×HCID 69902',4'-Dihydroxyacetophenone

Produkt 1

HCID 179274-Ethylresorcinol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysator2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

In a three necked round bottom flask (equipped with a condensor, additional funnel and mechanical stirrer) was added 15.2 g of a combination of Raney Nickel and Ni supported on silica. (50:50). 100 ml of a mixture of 50:50 ethanol:water was added and the reaction was heated at reflux conditions. 15.2 g of 2,4-dihydroxy acetophenone in 100 ml of water:ethanol and 10 ml of acetic acid was placed in the additional funnel and slowly added to the mixture (dropwise). The reaction was filtered through a milipore filter to give a pale yellow solution. Concentration of this solution in vacuo gave a solid. This solid was crystalized from 1,2-dichloroethane to give 4-ethyl resorcinol in 80% isolated yield. The unreacted 2,4-dihydroxy acetophenone was recovered (−17%) form the reaction mixture and was recycled. The structure of 4-ethyl resorcinol and 2,4-dihydroxy acetophenone were characterized by NMR, Gas Chromatography, IR and Mass spectroscopy

Aufarbeitung

  1. customIn a three necked round bottom flask (equipped with a condensor, additional funnel and mechanical stirrer)
  2. temperaturethe reaction was heated
  3. temperatureat reflux conditions
  4. additionslowly added to the mixture (dropwise)
  5. filtrationThe reaction was filtered through a milipore
  6. filtrationfilter
  7. customto give a pale yellow solution
  8. customConcentration of this solution in vacuo gave a solid
  9. customThis solid was crystalized from 1,2-dichloroethane

Quellen und Nachweise

ORD-Eintrag
ord-c2c86e4b6d864b08b6f3905698e551c8
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911562B2

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