Hydroquinone → 4-Methoxybicyclo[2.2.2]octan-2-one

HRID 259353

Reaktionsgleichung

Reaktionsgleichung von HRID 259353
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O.[C:20]([CH:23]1[CH2:28][CH2:27][C:26]([O:29][CH3:30])=[CH:25][CH2:24]1)(=[O:22])[CH3:21].C[O-].[Na+]>C1C=CC=CC=1.O>[CH3:30][O:29][C:26]12[CH2:27][CH2:28][CH:23]([CH2:24][CH2:25]1)[C:20](=[O:22])[CH2:21]2

Komponenten

7

Edukt 4

HCID 785HydroquinoneHCID 6101p-Toluenesulfonic acidHCID 10942334Sodium MethoxideHCID 203422181-Acetyl-4-methoxy-3-cyclohexene

Produkt 1

HCID 5663034-Methoxybicyclo[2.2.2]octan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 13.2 g. of p-toluenesulfonic acid and 0.9 g. of hydroquinone in 540 ml. of benzene was heated at reflux under a Dean Stark trap until no more water was evolved. A solution of 90.6 g. of 1-Acetyl-4-methoxy-3-cyclohexene in 750 ml. of benzene was then added to the refluxing solution over 6 hrs. Following an additional hr's heating the mixture was cooled and treated with 16 ml. of 4.64 N methanolic sodium methoxide. The mixture was washed twice with water and the solvent evaporated in vacuum. The residual oil was distilled at 0.45 mm to afford 64.2 g. of bicyclic ketone 4-Methoxybicyclo[2,2,2]-octan-2-one, bp 77°-82°.

Aufarbeitung

  1. additionA mixture of 13.2 g
  2. temperatureheating the mixture
  3. temperaturewas cooled
  4. additiontreated with 16 ml
  5. washThe mixture was washed twice with water
  6. customthe solvent evaporated in vacuum
  7. distillationThe residual oil was distilled at 0.45 mm
  8. customto afford 64.2 g

Quellen und Nachweise

ORD-Eintrag
ord-29ea36d01e00401692aba3af066ec3ac
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04036977

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