1,5-Dibromopentane → 1-[3-[(5-Bromopentyl)oxy]propyl]-4-methoxybenzene

HRID 1534911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534911
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1.[Br: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:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:12][CH2:11][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 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 794063-(4-Methoxyphenyl)-1-propanol

Produkt 1

HCID 197980251-[3-[(5-Bromopentyl)oxy]propyl]-4-methoxybenzeneAusbeute 244,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

4-Methoxybenzenepropanol (7.5 g) and 1,5 dibromopentane (30.5 g) were stirred rapidly at RT with tetra-n-butylammonium bisulphate (1.02 g) and 12.5M aqueous NaOH (36 ml) for 16 h. The mixture was diluted with H2O (170 ml), extracted with ER (3×200 ml) and the combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml), dried and evaporated to give an oil (34.8 g). The oil was purified by [FCS] eluting with ER-CX (0:100→4:96) to give the title compound as a colourless oil (8.83 g). T.l.c. (CX-ER 79:1) Rf 0.1.

Aufarbeitung

  1. extractionextracted with ER (3×200 ml)
  2. washthe combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml)
  3. customdried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d495e9e77248453fa5782c04808d0ae1
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05091422

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