Acetic Acid → 4-(N-phenylbenzylamino)benzaldehyde

HRID 1058660

Reaction equation

HRID 1058660 reaction equation
[C:1]1([N:7]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O.[C:24](O)(=[O:26])C>>[C:1]1([N:7]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:8]2[CH:13]=[CH:12][C:11]([CH:24]=[O:26])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69080Benzyldiphenylamine

Product 1

HCID 99657034-(N-phenylbenzylamino)benzaldehydeYield 72%

Conditions

Temperature
90 °C

Procedure

N,N-diphenylbenzylamine (935 mg, 3.60 mmol) was suspended in acetic acid (20 mL), and hexamethylenetriamine (1.12 g, 7.96 mmol) was added thereto, followed by stirring at 90° C. for 12 hours. The reaction liquid was cooled to room temperature, a 6 mol/L sodium hydroxide aqueous solution and water were added thereto, and then the product was extracted with chloroform. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=20/1→10/1), to obtain 4-(N-phenylbenzylamino)benzaldehyde (742 mg, 72%).

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. extractionthe product was extracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=20/1→10/1)

Sources & evidence

ORD record
ord-1e78f384f28e427db5a5c7b5e8f59a82
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Linked notes

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