Hydrochloric Acid → 4-(Ethyl(2-hydroxyethyl)amino)benzaldehyde

HRID 983575

Reaction equation

HRID 983575 reaction equation
[OH-].[Na+].[CH2:3]([N:5]([CH2:14][CH2:15][O:16]C(=O)C)[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][CH:7]=1)[CH3:4].Cl>C(O)C>[CH2:3]([N:5]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]=[O:13])=[CH:10][CH:11]=1)[CH2:14][CH2:15][OH:16])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11458991Benzaldehyde, 4-[[2-(acetyloxy)ethyl]ethylamino]-

Product 1

HCID 6398574-(Ethyl(2-hydroxyethyl)amino)benzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A 150 ml of NaOH-solution (5 M in water) is added to a solution of 59.2 g (252 mmol) of 17 in 200 ml of ethanol and the mixture is stirred overnight at 40° C. The reaction mixture is cooled in an ice bath and neutralized with HCl (5 M) and extracted with dichloromethane. The organic layer is washed with a saturated NaHCO3-solution, with brine and dried over MgSO4. The solvents are evaporated under reduced pressure. The product is isolated as an oil and used without further purification.

Workup

  1. temperatureThe reaction mixture is cooled in an ice bath
  2. extractionextracted with dichloromethane
  3. washThe organic layer is washed with a saturated NaHCO3-solution, with brine
  4. dry with materialdried over MgSO4
  5. customThe solvents are evaporated under reduced pressure
  6. customThe product is isolated as an oil
  7. customused without further purification

Sources & evidence

ORD record
ord-067bfc77490a46de92e6cddc0813553f
Source dataset
uspto-grants-2005_03
Patent number
US06864347B2

Linked notes

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