Hydrochloric Acid → 2-Isopropyl-4,5-dimethoxy-benzaldehyde

HRID 38328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38328
[CH:1]([C:4]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:5]=1[CH:6]=NC(C(C)C)C(C)C)([CH3:3])[CH3:2].Cl.C1C[O:27]CC1>>[CH:1]([C:4]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:5]=1[CH:6]=[O:27])([CH3:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 59598696(2-Isopropyl4,5-dimethoxy-benzylidene)-(1-isopropyl-2-methyl-propyl)-amine

Produkt 1

HCID 541451142-Isopropyl-4,5-dimethoxy-benzaldehydeAusbeute 43 %

Versuchsvorschrift

(2-Isopropyl-4,5-dimethoxy-benzylidene)-(1-isopropyl-2-methyl-propyl)-amine was dissolved in 30 ml of THF. HCl (4.1 mL, 4 M) was added and the mixture was warmed to reflux. After 3 hours the mixture was cooled concentrated in vacuo. 100 mL of H2O was added and the mixture was extracted with ethyl acetate, washed with H2O and then with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give an orange oil. Purification via flash chromatography (85:15 hexane/ethyl acetate) gave 2-isopropyl-4,5-dimethoxy-benzaldehyde (0.331 g, 43%) as a clear oil

Aufarbeitung

  1. temperaturethe mixture was warmed to reflux
  2. temperatureAfter 3 hours the mixture was cooled
  3. concentrationconcentrated in vacuo
  4. addition100 mL of H2O was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with H2O
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give an orange oil
  11. customPurification via flash chromatography (85:15 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b1dcbef1739948fe87cc9c46b0f68caa
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524725B2

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