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

HRID 1721906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1721906
[CH3:1][S: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+]>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]([S:2][CH3:1])=[CH:4][CH:5]=1

Komponenten

5

Edukt 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 27600862-(4-Methylsulfanylphenyl)ethanol

Produkt 1

HCID 200713861-[2-[(5-Bromopentyl)oxy]ethyl]-4-(methylthio)benzeneAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4-(Methylthio)benzeneethanol (7.44 g) and 1,5 dibromopentane (30.48 g) were stirred rapidly at room temperature with TAB (1.0 g) and 12.5M aqueous sodium hydroxide (35 ml) for 64 h. The mixture was diluted with water (170 ml), extracted with ER (3×200 ml) and the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml), dried and evaporated. The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97) to give the title compound as a colourless oil (10.68 g). T.l.c. (ER-CX 1:79) Rf 0.08.

Aufarbeitung

  1. extractionextracted with ER (3×200 ml)
  2. washthe combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml)
  3. customdried
  4. customevaporated
  5. customThe residual oil (29.29 g) was purified by FCC
  6. washeluting with ER-CX (0:100→3:97)

Quellen und Nachweise

ORD-Eintrag
ord-ba1bab03dff0470598d639f62f112036
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04853382

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