N,N-Dihexylaniline → Benzaldehyde, 4-(dihexylamino)-

HRID 1250007Notes

Reaction equation

HRID 1250007 reaction equation
[CH2:1]([N:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C[C:21]([O-])=[O:22].[Na+]>CN(C=O)C>[CH2:14]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]1[CH:9]=[CH:10][C:11]([CH:21]=[O:22])=[CH:12][CH:13]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 138236N,N-DihexylanilineHCID 517045Sodium Acetate

Product 1

HCID 11289255Benzaldehyde, 4-(dihexylamino)-Yield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of dry DMF (1.1. mL) under Argon at 0° C. was added of POC13(375 μL, 4 mmol). N,N-Dihexylaniline (1.04 g, 4 mmol) was added dropwise and the solution was mixed with rapid stirring to form a green solution. The reaction mixture was heated at 95° C. for 2 h. The solution quickly turned red/brown. After 2 h the solution was cooled. It was poured into ice/water 20 mL and aq. saturated NaOAc (20 mL) was added. The partially neutralized solution was partitioned between ether and water. The ether layer was washed with aq. saturated NaHCO3 and dried over sodium sulfate. After concentrating to approximately 20 mL. DMF oiled out of the solution. The solution was transferred from the oil and concentrated under reduced pressure. The resultant residue was purified via flash column chromatography, using a gradient of 0→20% ethyl acetate; petroleum ether as eluent to give N,N-Dihexyl-4-aminobenzaldehyde (32) (970 mg, 84%). 1H NMR (CDCl3) δ 9.72 (s, 1H CHO); 7.70 (d, 2H, ArH); 6.64 (d, 2H, ArH); 3.32 (t, 4H, 2×NCH2); 0.89 (t, 6H 2×CH2CH3). TLC (silica gel): Rf=0.75 (20% ethyl acetate;petroleum ether).

Workup

  1. additionthe solution was mixed
  2. customto form a green solution
  3. temperatureAfter 2 h the solution was cooled
  4. additionwas added
  5. customThe partially neutralized solution was partitioned between ether and water
  6. washThe ether layer was washed with aq. saturated NaHCO3
  7. dry with materialdried over sodium sulfate
  8. concentrationAfter concentrating to approximately 20 mL
  9. concentrationconcentrated under reduced pressure
  10. customThe resultant residue was purified via flash column chromatography

Sources & evidence

ORD record
ord-93f6bf38082948faa7413db6be6624de
Source dataset
uspto-grants-2002_01
Patent number
US06335446B1

Reaction notes

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