Acetic Acid → 4-Ethyl-1,2-benzenediol

HRID 703999

Reaktionsgleichung

Reaktionsgleichung von HRID 703999
[CH2:1]([C:3]1[CH:4]=[C:5]([O:11]C)[C:6]([O:9]C)=[CH:7][CH:8]=1)[CH3:2].C(O)(=O)C.Br.O>CCOCC>[CH2:1]([C:3]1[CH:4]=[C:5]([OH:11])[C:6](=[CH:7][CH:8]=1)[OH:9])[CH3:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 962WaterHCID 799904-Ethyl-1,2-dimethoxybenzene

Produkt 1

HCID 707614-Ethyl-1,2-benzenediolAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 10.0 g (60.2 mM) of 4-ethylveratrole, 38.4 g (639 mM) of acetic acid and 115.0 g (668 mM) of 47% hydrobromic acid was heated under reflux for 4 hours with stirring After cooling to the room temperature, 100 ml of water was added and the resultant mixture was extractbd three times with each 110 ml of ether. The ether extract was successively washed with 110 ml of water, 150 g of 5% aqueous sodium thiosulfate solution and further twice with each 110 ml of water. The resulting ether solution was dried with anhydrous sodium sulfate, filtered, concentrated and distilled under vacuum to obtain 7.4 g (53.6 mM) of 4-ethylcatechol as a light yellow liquid having a boiling point of 111°-112 ° C./4 mmHg.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. additionwas added
  4. extractionThe ether extract
  5. washwas successively washed with 110 ml of water, 150 g of 5% aqueous sodium thiosulfate solution and further twice with each 110 ml of water
  6. dry with materialThe resulting ether solution was dried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. distillationdistilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f7d8572ab14b44c9b42d6045c0a96503
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04985458

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