1-Bromo-3-chloropropane → 8-Hydroxyjulolidine

HRID 2303942

Reaktionsgleichung

Reaktionsgleichung von HRID 2303942
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][CH2:11][CH2:12]Cl.[Na+].[CH2:15]([C:27]1C=CC=CC=1S([O-])(=O)=O)[CH2:16]CCCCCCCCCC>O>[CH2:11]1[CH2:12][N:1]2[C:2]3[C:3]([CH2:16][CH2:15][CH2:27]2)=[C:4]([OH:8])[CH:5]=[CH:6][C:7]=3[CH2:10]1

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 115683-AminophenolHCID 23662403Sodium Dodecylbenzenesulfonate

Produkt 1

HCID 1704748-HydroxyjulolidineAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

According to a procedure similar to that of Embodiment 1, a mixture of m-aminophenol (116 mg, 1 mmol), 1-bromo-3-chloropropane (0.48 g, 0.3 ml, 3 mmol), dodecylbenzenesulfonic acid sodium salt (349 mg, 1 mmol) and a buffer solution prepared by dissolving 1.50 g (4 mmol) of Na2HPO4 12H2O and 0.60 g (4 mmol) of NaH2PO42H2O in water (10 ml) was heated and refluxed for 12 hours. After silica gel column chromatography, 8-hydroxyjulolidine (28 mg) was obtained in 15% yield.

Aufarbeitung

  1. customa buffer solution prepared
  2. temperaturewas heated
  3. temperaturerefluxed for 12 hours

Quellen und Nachweise

ORD-Eintrag
ord-59084fd80546448daa29639f10b222b3
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06433176B1

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