1,6-Dibromohexane → 1-[2-[(6-Bromohexyl)oxy]ethyl]-4-methoxybenzene

HRID 483470

Reaktionsgleichung

Reaktionsgleichung von HRID 483470
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Komponenten

6

Edukt 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 697054-Methoxyphenethyl alcohol

Produkt 1

HCID 197980401-[2-[(6-Bromohexyl)oxy]ethyl]-4-methoxybenzeneAusbeute 237,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

4-Methoxybenzeneethanol (5.0 g) and 1,6-dibromohexane (23.7 g) were stirred rapidly at RT with tetra-n-butyl ammonium bisulphate (0.94 g) and 12.5M aqueous NaOH (30 ml) for 16 h. The mixture was diluted with H2O (125 ml), extracted with ER (3×150 ml) and the combined organic extracts were washed consecutively with H2O (125 ml), BR (125 ml), dried and evaporated to give an oil (24.6 g). The oil was purified by [FCS] eluting with ER-CX (0:100→4:96) to give the title compound as a colourless oil (8.30 g). T.l.c. (CX-ER (40:1)) Rf 0.33.

Aufarbeitung

  1. extractionextracted with ER (3×150 ml)
  2. washthe combined organic extracts were washed consecutively with H2O (125 ml), BR (125 ml)
  3. customdried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d44c00381d374bc1acaf524fe3d58110
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05225445

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