Water → 2-phthalimido-acetophenone

HRID 1296193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1296193
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K].O>CN(C=O)C>[C:11]1(=[O:21])[N:15]([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12

Komponenten

5

Edukt 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 2430382-phthalimido-acetophenoneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of 2-bromoacetophenone (30.0 g, 151 mmol) in DMF (120 ml) was treated with potassium phthalimide (30.8 g, 166 mmol) portionwise at ambient temperature, and then heated to 40° C. for 3.5 hr. The cooled mixture was poured into water (600 ml) and extracted with chloroform (300 ml then 100 ml). The combined organic phases were washed with sodium hydroxide (200 ml, 0.2 N), water (2×100 ml) and brine (100 ml), dried over magnesium sulfate and concentrated in vacuo. The resulting cream solid was suspended in ether (100 ml), recovered by filtration, washed with ether (100 ml) and dried in vacuo to yield pure 2-phthalimido-acetophenone as a white solid (34.3 g, 86%).

Aufarbeitung

  1. extractionextracted with chloroform (300 ml
  2. washThe combined organic phases were washed with sodium hydroxide (200 ml, 0.2 N), water (2×100 ml) and brine (100 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationrecovered by filtration
  6. washwashed with ether (100 ml)
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0a77361d9d1047db8eeb409ef7332cb0
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244851B2

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