Ethylene Glycol → N-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl}phthalimide

HRID 704910Notes

Reaction equation

HRID 704910 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])=[O:2].[CH2:24](O)[CH2:25][OH:26].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[O:2]1[CH2:24][CH2:25][O:26][CH:1]1[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:11](=[O:20])[C:12]2=[CH:19][CH:18]=[CH:17][CH:16]=[C:13]2[C:14]1=[O:15]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 128106403-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)benzaldehyde

Product 1

HCID 14086555N-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl}phthalimideYield 92.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-[3-(3-formylphenoxy)propyl]phthalimide (29 g) was dissolved in 400 ml of benzene, and 11.67 g of ethylene glycol and 1.8 g of p-toluenesulfonic acid were added, and the mixture was heated under reflux for 7 hours while water was removed by using a Dean-Stark trap. After the reaction, the reaction mixture was cooled and the benzene layer was washed successively with a 1N aqueous NaOH solution, water, and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 30.63 g (yield 92%) of N-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl}phthalimide.

Workup

  1. temperaturethe mixture was heated
  2. customwas removed
  3. customAfter the reaction
  4. temperaturethe reaction mixture was cooled
  5. washthe benzene layer was washed successively with a 1N aqueous NaOH solution, water
  6. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3c8da79a30b04c86aaf1d5332fae1a7f
Source dataset
uspto-grants-1991_01
Patent number
US04988828

Reaction notes

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