Acetic Acid → 4-Propyl-1,2-benzenediol

HRID 249261

Reaktionsgleichung

Reaktionsgleichung von HRID 249261
[CH2:1]([C:4]1[CH:5]=[C:6]([O:12]C)[C:7]([O:10]C)=[CH:8][CH:9]=1)[CH2:2][CH3:3].C(O)(=O)C.Br>O>[CH2:1]([C:4]1[CH:5]=[C:6]([OH:12])[C:7](=[CH:8][CH:9]=1)[OH:10])[CH2:2][CH3:3]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 1232331,2-Dimethoxy-4-propylbenzene

Produkt 1

HCID 976384-Propyl-1,2-benzenediolAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 15.0 g (83 mM) of 4-propylveratrole, 53.0 g (882 mM) of acetic acid and 159.4 g (926 mM) of 47% hydrobromic acid was heated under reflux for 2 hours with stirring. After cooling to the room temperature, the reaction mixture was added with 140 ml of water and extracted three times with each 150 ml of ether. The extracted ether solution was successively washed with 150 ml of water, 150 g of 5% aqueous sodium thiosulfate solution and then twice with each 150 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether and vacuum distilled to obtain 10.5 g (69 mM) of 4-propylcatechol as a light yellow liquid having a boiling point of 119° C/3 mmHg.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted three times with each 150 ml of ether
  4. washThe extracted ether solution was successively washed with 150 ml of water, 150 g of 5% aqueous sodium thiosulfate solution
  5. dry with materialThe resulting solution was dried with anhydrous sodium sulfate
  6. distillationdistilled off ether and vacuum
  7. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-3cbccf9ce7784f9ab1f060329f82414f
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05214034

Verknüpfte Notizen

Wird geladen…