Water → 2-(6-hydroxyhexyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1449432

Reaktionsgleichung

Reaktionsgleichung von HRID 1449432
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K].C(OCC)(=O)C.O>CN(C)C=O>[OH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:13]1[C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]2[C:9]1=[O:19]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 779706-Bromo-1-hexanolHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 129502192-(6-hydroxyhexyl)-2,3-dihydro-1H-isoindole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Bromohexan-1-ol (8 g, 44 mmol) and potassium phthalimide (16.4 g, 88 mmol) were heated at 90° C. for two hours in dry N,N-dimethylformamide (50 ml). The mixture was cooled and partitioned between chloroform (150 ml) and water (150 ml). The organic layer washed with water (2×150 ml), dried over anhydrous magnesium sulphate, filtered, and the filtrate evaporated under reduced pressure to give a yellow liquid. The liquid was left at 4° C. for 72 hours before repartitioning between ethyl acetate (150 ml) and water (150 ml). The organic layer was washed with water (2×150 ml), dried over anhydrous magnesium sulphate, filtered, and the filtrate evaporated under reduced pressure. Diethyl ether was added and following cooling the solid was removed by filtration. The process was repeated and the liquors were evaporated to give N-(6-hydroxyhexyl)-phthalimide. 1H-NMR: (60 MHz) (CDCl3), δ 7.7 (4H,s), 3.6 (5H,m) and 1.4 (8H,m) ppm

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. custompartitioned between chloroform (150 ml) and water (150 ml)
  3. washThe organic layer washed with water (2×150 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customto give a yellow liquid
  8. washThe organic layer was washed with water (2×150 ml)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. filtrationfiltered
  11. customthe filtrate evaporated under reduced pressure
  12. additionDiethyl ether was added
  13. temperaturefollowing cooling the solid
  14. customwas removed by filtration
  15. customthe liquors were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-7dbf8d863d50477e9ebbd5cc579ec244
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599587

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