Hydrochloric Acid → 1,2-Bis(3,4-dimethoxyphenyl)ethanone

HRID 1954048

Reaktionsgleichung

Reaktionsgleichung von HRID 1954048
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][C:26](Cl)=[O:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].Cl>>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([C:26]([CH2:25][C:19]2[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:17]([O:16][CH3:15])[CH:18]=2)=[O:27])[CH:10]=[CH:9][C:8]=1[O:13][CH3:14]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 7043VeratroleHCID 3604458(3,4-Dimethoxyphenyl)acetyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 2311111,2-Bis(3,4-dimethoxyphenyl)ethanoneAusbeute 98 %

Versuchsvorschrift

Powdered anhydrous aluminum chloride (0.78 g) was slowly added to a stirred mixture of 1,2-dimethoxybenzene (0.64 g, 4.66 mmol) and 3,4-dimethoxyphenylacetyl chloride (1.0 g, 4.66 mmol) in 10 mL freshly distilled dry dichloromethane. An exothermic reaction occurred. The orange solution became brown as the mixture refluxed. The reaction mixture was heated to reflux for an additional 2 h and then allowed to cool to room temperature. The cooled solution was poured into a mixture containing of 5 g crushed ice and 5.5 mL 7.5 N HCl. The organic phase was separated and the aqueous phase was extracted three times with 10 mL dichloromethane. The combined dichloromethane extract was dried (Na2SO4), filtered, and evaporated to give a white solid, which was crystallized from ethanol to give pure white needles of 11a in 98% yield; mp 105-107° C. (lit.30 mp 104-106° C.); 1H NMR δ 3.85 (s, 6H), 3.91 (s, 3H), 3.94 (s, 3H), 4.18 (s, 2H), 6.81 (m, 2H), 6.91 (m, 2H), 7.56 (d, 1H, J=2.0), 7.66 (dd, 1H, J=8.4,2.0); 13C NMR δ 45.2, 56.3, 56.4, 56.5, 110.4, 111.1, 111.8, 112.8, 121.3, 121.9, 123.9, 127.9, 130.2, 148.4, 149.5, 153.8, 197.0.

Aufarbeitung

  1. distillationfreshly distilled dry dichloromethane
  2. customAn exothermic reaction
  3. temperaturerefluxed
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux for an additional 2 h
  6. additionThe cooled solution was poured into a mixture
  7. additioncontaining of 5 g
  8. customThe organic phase was separated
  9. extractionthe aqueous phase was extracted three times with 10 mL dichloromethane
  10. extractionThe combined dichloromethane extract
  11. dry with materialwas dried (Na2SO4)
  12. filtrationfiltered
  13. customevaporated
  14. customto give a white solid, which
  15. customwas crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0055ae4d18f74f75912e8ca592f59415
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06121275

Verknüpfte Notizen

Wird geladen…