1-Hexanol → 3-(Hexyloxy)thiophene

HRID 2106896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2106896
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][S:5][CH:4]=1.[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12]C.OS([O-])(=O)=O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:2][C:3]1[CH:7]=[CH:6][S:5][CH:4]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Komponenten

5

Edukt 3

HCID 81031-HexanolHCID 1402493-MethoxythiopheneHCID 516919Sodium Bisulfate

Produkt 1

HCID 110414173-(Hexyloxy)thiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

20 cm3 of 3-methoxythiophene (0.2 mol) and 50 cm3 of 1-hexanol were dissolved in 30 cm3 of toluene, and 1 g of NaHSO4 (0.01 mol) was added. The mixture was heated to 125° C. and stirred, and about 10 cm3 of a mixture of methanol and toluene were distilled off through a Vigreux column at a head temperature of 63° to 64° C., which took about 3 hours. The mixture was then washed three times with 50 cm3 of saturated NaHCO3 solution until neutral, dried over MgSO4 and fractionated in vacuo. After the toluene had been distilled off together with excess haxanol, 34 g of 3-n-hexyloxythiophene distilled over at 70° C. and 0.13 mbar, which corresponds to 92% of the theoretical yield. 97% pure by GC; 1H-NMR and mass spectrum confirm the structure.

Aufarbeitung

  1. distillationabout 10 cm3 of a mixture of methanol and toluene were distilled off through a Vigreux column at a head temperature of 63° to 64° C., which
  2. washThe mixture was then washed three times with 50 cm3 of saturated NaHCO3 solution until neutral,
  3. dry with materialdried over MgSO4
  4. distillationAfter the toluene had been distilled off together with excess haxanol, 34 g of 3-n-hexyloxythiophene
  5. distillationdistilled over at 70° C. and 0.13 mbar, which

Quellen und Nachweise

ORD-Eintrag
ord-6a040e908a4442d8a5cfd1d4e676defb
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04931568

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