Sulfuric Acid → 4-Acetamidobutanal

HRID 1414704Notes

Reaction equation

HRID 1414704 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:11])[CH3:10])C.S(=O)(=O)(O)O>O>[C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH:4]=[O:3])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12677171N-(4,4-diethoxybutyl)acetamide

Product 1

HCID 4408504-Acetamidobutanal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve 5 gms. of 4-acetamidobutyraldehyde diethyl acetal in 75 ml. of distilled water and 5 ml. of 1 N sulfuric acid. Allow the solution to stand at room temperature until the hydrolysis is complete as determined by thin layer chromatography. Neutralize the solution with sodium bicarbonate, then saturate the solution with sodium chloride and extract with chloroform. Distill the combined chloroform extracts to a residue comprising 4-acetamidobutyraldehyde, which can be used without further purification in the following procedure.

Workup

  1. dissolutionDissolve 5 gms
  2. customto stand at room temperature until the hydrolysis
  3. concentrationNeutralize the solution with sodium bicarbonate, then saturate the solution with sodium chloride
  4. extractionextract with chloroform
  5. distillationDistill the combined chloroform
  6. customcan be used without further purification in the following procedure

Sources & evidence

ORD record
ord-ce6a1a168afa4d6c89aabae2520447be
Source dataset
uspto-grants-1977_01
Patent number
US04002608

Reaction notes

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