Benzene → 2,6-Dimethoxy-4-methylidenecyclohexa-2,5-dien-1-one

HRID 1632444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1632444
[CH3:1][O:2][C:3]1[C:4](=[O:14])[C:5]([O:12][CH3:13])=[CH:6][C:7](OC)([CH3:9])[CH:8]=1.C1C=CC=CC=1.C(=O)([O-])O.[Na+]>S(=O)(=O)(O)O>[CH3:13][O:12][C:5]1[C:4](=[O:14])[C:3]([O:2][CH3:1])=[CH:8][C:7](=[CH2:9])[CH:6]=1

Komponenten

5

Edukt 3

HCID 241BenzeneHCID 516892Sodium BicarbonateHCID 13229516HCID 13229516, Verbindung

Produkt 1

HCID 132295172,6-Dimethoxy-4-methylidenecyclohexa-2,5-dien-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A 198 mg quantity of 2,4,6-trimethoxy-4-methyl-2,5-cyclohexadienone and 10 ml of benzene were dissolved in 10 ml of concentrated sulfuric acid, and stirred at room temperature for 2 hours. Thereafter the solution was neutralized by adding sodium hydrogen carbonate to the solution and filtered. The filtrate was concentrated at reduced pressure. The residue was extracted with dichloromethane, the solvent was removed at reduced pressure and the resulting residue was concentrated, thereby recovering 158 mg of an oily crude product. The crude product was purified by silica gel column chromatography using a 20:1 benzene-ethyl acetate mixture, giving 153 mg of 2,6-dimethoxy-4-methylidene-2,5-cyclohexadienone in 92% of theoretical yield. The compound thus obtained was identified by NMR.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated at reduced pressure
  3. extractionThe residue was extracted with dichloromethane
  4. customthe solvent was removed at reduced pressure
  5. concentrationthe resulting residue was concentrated
  6. customrecovering 158 mg of an oily crude product
  7. customThe crude product was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-808988a8a6c1445c8a9725ca53d1da06
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04475992

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