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

HRID 704910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 704910
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 14086555N-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl}phthalimideAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3c8da79a30b04c86aaf1d5332fae1a7f
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988828

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