Ethylene Glycol → Dibenzyl-(4-[1,3]dioxolan-2-yl-2,5-dimethyl-phenyl)amine

HRID 1361724Notes

Reaction equation

HRID 1361724 reaction equation
Cl.[CH2:2]([N:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]1[C:17]([CH3:18])=[CH:16][C:13]([CH:14]=[O:15])=[C:12]([CH3:19])[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:27](O)[CH2:28][OH:29].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:20]([N:9]([CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:10]1[CH:11]=[C:12]([CH3:19])[C:13]([CH:14]2[O:29][CH2:28][CH2:27][O:15]2)=[CH:16][C:17]=1[CH3:18])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 57461073HCID 57461073, compound

Product 1

HCID 57461075Dibenzyl-(4-[1,3]dioxolan-2-yl-2,5-dimethyl-phenyl)amineYield 97.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 500 mL round-bottomed flask was added 4-dibenzylamino-2,5-dimethylbenzaldehyde hydrochloride (11.5 g, 31.4 mmol) and toluene (150 mL) and the resulting mixture was stirred until the salt completely dissolved. The reaction flask was then purged with dry nitrogen for 5 minutes. Ethylene glycol (5.25 mL, 94.2 mmol) and p-toluenesulfonic acid (760 mg, 6.2 mmol) were added and the resulting mixture was heated at 60° C. to 80° C. for about 20 hours. The solvent was then removed slowly (over about 40 minutes) at 40° C. on a rotary evaporator. Toluene (100 mL) was added to the residue and the solvent was again removed slowly at 40° C. on a rotary evaporator. This process was repeated using another aliquot of toluene (100 mL) and the mixture was evaporated to dryness. Ethyl acetate (150 mL) and saturated aqueous sodium bicarbonate (100 mL) were added to the residue and the layers were separated. The organic layer was washed with brine (50 mL) and then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide crude dibenzyl-(4-[1,3]dioxolan-2-yl-2,5-dimethyl-phenyl)amine (11.4 g).

Workup

  1. dissolutioncompletely dissolved
  2. customThe reaction flask was then purged with dry nitrogen for 5 minutes
  3. temperaturethe resulting mixture was heated at 60° C. to 80° C. for about 20 hours
  4. customThe solvent was then removed slowly (over about 40 minutes) at 40° C.
  5. customon a rotary evaporator
  6. additionToluene (100 mL) was added to the residue
  7. customthe solvent was again removed slowly at 40° C. on a rotary evaporator
  8. customthe mixture was evaporated to dryness
  9. additionEthyl acetate (150 mL) and saturated aqueous sodium bicarbonate (100 mL) were added to the residue
  10. customthe layers were separated
  11. washThe organic layer was washed with brine (50 mL)
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5a6612bb1d848cba8360a1065ddcd5f
Source dataset
uspto-grants-2011_02
Patent number
US07880010B2

Reaction notes

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