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

HRID 1627983Notes

Reaction equation

HRID 1627983 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 552846924-Amino-2,5-dimethylbenzaldehydeYield 22.8%

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst

Conditions

Temperature
90 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ec3bafc94f814d3ebc3cd16ce5a90227
Source dataset
uspto-grants-2014_07
Patent number
US08785692B2

Reaction notes

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