1,5-Dibromopentane → 1-[2-[(5-Bromopentyl)oxy]ethyl]-4-methoxybenzene

HRID 1084962

Reaktionsgleichung

Reaktionsgleichung von HRID 1084962
[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]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][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 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 697054-Methoxyphenethyl alcohol

Produkt 1

HCID 200628301-[2-[(5-Bromopentyl)oxy]ethyl]-4-methoxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-methoxybenzeneethanol (7.0 g), 1,5-dibromopentane (20 ml), 50% aqueous sodium hydroxide (30 ml) and tetrabutylammonium bisulphate (1 g) was stirred at room temperature overnight, water (100 ml) wa added and the mixture was extracted with ER (2×100 ml). The organic extracts were washed with water and brine, dried and concentrated in vacuo to give an oil which was purified by FCC eluting with hexane→hexane-ER (9:1) to give the title compound as a colourless liquid (10.5 g). T.l.c. hexane-ER (9:1) Rf 0.28.

Aufarbeitung

  1. extractionthe mixture was extracted with ER (2×100 ml)
  2. washThe organic extracts were washed with water and brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give an oil which
  6. customwas purified by FCC
  7. washeluting with hexane→hexane-ER (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-480c9ad7458d45a7aff014d7786fa990
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05006556

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