Hydrochloric Acid → 4-Amino-2,5-dimethylbenzaldehyde

HRID 2194339

Reaktionsgleichung

Reaktionsgleichung von HRID 2194339
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].Cl.[OH-:11].[Na+].[CH3:13]S(C)=O>[Cu](Cl)Cl>[NH2:4][C:3]1[C:2]([CH3:1])=[CH:8][C:7]([CH:13]=[O:11])=[C:6]([CH3:9])[CH:5]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 72592,5-DimethylanilineHCID 14798Sodium Hydroxide

Produkt 1

HCID 552846924-Amino-2,5-dimethylbenzaldehydeAusbeute 22,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24014Cupric ChlorideKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

6.06 g (50.0 mmol) of 2,5-dimethylaniline are initially charged in 1000 ml of DMSO, 13.55 g (100.0 mmol) of copper(II) chloride are added and concentrated hydrochloric acid is then added slowly. The reaction mixture is heated at 90° C. for 3 h and then added to ice-water. After addition of aqueous sodium hydroxide solution, the mixture is filtered and extracted repeatedly with ethyl acetate, and the combined organic phases are dried over Na2SO4 and freed from solvent under reduced pressure. The crude product is purified by column chromatography. (2.27 g, purity 75.0%, yield 22.8%, log P (pH 2.3)=1.34).

Aufarbeitung

  1. filtrationthe mixture is filtered
  2. extractionextracted repeatedly with ethyl acetate
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. customThe crude product is purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ba5b549cf843458db48e0963abeacaa2
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334237B2

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