Ethylene Glycol → 4-(1,3-Dioxolan-2-yl)aniline

HRID 433335Notes

Reaction equation

HRID 433335 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-])=O.[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[NH2:1][C:4]1[CH:11]=[CH:10][C:7]([CH:8]2[O:14][CH2:13][CH2:12][O:9]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 5414-NitrobenzaldehydeHCID 962WaterHCID 6101p-Toluenesulfonic acid

Product 1

HCID 111266244-(1,3-Dioxolan-2-yl)aniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 4-nitrobenzaldehyde (7.55 g, 50 mmol) and ethyleneglycol (4.65 g, 75.0 mmol) in toluene (125 ml) was added 4-toluenesulphonic acid (100 mg, 0.5 mmol) and the mixture heated under reflux using a Dean-Stark water separator for 2 h. The solution was evaporated to dryness, the residue dissolved in EtOAc (125 ml), washed with saturated sodium hydrogen carbonate solution, dried and evaporated to dryness. The residue was dissolved in ethanol (200 ml) and hydrogenated over 10% Pd/C for 4 h at ambient temperature. The catalyst was removed by filtration, the ethanol evaporated to yield the title compound which was used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux
  3. customThe solution was evaporated to dryness
  4. dissolutionthe residue dissolved in EtOAc (125 ml)
  5. washwashed with saturated sodium hydrogen carbonate solution
  6. customdried
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in ethanol (200 ml) and hydrogenated over 10% Pd/C for 4 h at ambient temperature
  9. customThe catalyst was removed by filtration
  10. customthe ethanol evaporated

Sources & evidence

ORD record
ord-8129d99fab114863adc3707f554e2346
Source dataset
uspto-grants-2003_12
Patent number
US06667342B1

Reaction notes

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