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

HRID 1651342Notes

Reaction equation

HRID 1651342 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]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=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

5

Reactant 2

HCID 174Ethylene GlycolHCID 128106403-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)benzaldehyde

Product 1

HCID 14086555N-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl}phthalimideYield 112.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

To a solution of N-[3-(3-formylphenoxy)propyl]phthalimide (92.8 g, 0.3 mole), ethylene glycol (44 mL, 0.8 mole) in benzene (1.5 L) was added 3 g of p-toluenesulfonic acid and the mixture was refluxed under a Dean-Stark trap for 14 hours. The cooled mixture was extracted with 100 mL of saturated aqueous sodium bicarbonate and then with 200 mL of saturated aqueous sodium chloride. The organic phase was dried and evaporated under reduced pressure to give 119.4 g of the title compound which crystallized on standing.

Workup

  1. temperaturethe mixture was refluxed under a Dean-Stark trap for 14 hours
  2. extractionThe cooled mixture was extracted with 100 mL of saturated aqueous sodium bicarbonate
  3. customThe organic phase was dried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dd5119172e2548ba89fc0b5f398ca96a
Source dataset
uspto-grants-1990_05
Patent number
US04927968

Reaction notes

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