1-Hexanol → 2-(Hexyloxy)thiophene

HRID 2106899Notes

Reaction equation

HRID 2106899 reaction equation
[CH3:1][O:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.OS([O-])(=O)=O.[Na+].[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18]C>C1(C)C=CC=CC=1>[CH2:1]([O:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 81031-HexanolHCID 856102-MethoxythiopheneHCID 516919Sodium Bisulfate

Product 1

HCID 144732252-(Hexyloxy)thiopheneYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

15 cm3 of 2-methoxythiophene were dissolved in 40 cm3 of n-hexanol and 30 cm3 of toluene, 1 g of NaHSO4 was added, and the mixture was refluxed for several hours. After distilling off 6 cm3 of an azeotrope of methanol and toluene, the residue was washed with sodium carbonate solution, dried and fractionated. 18 g of 2-hexyloxythiophene of b.p. 66° C./0.26 mbar were distilled off, 96% pure. Yield 65% of theory.

Workup

  1. temperaturethe mixture was refluxed for several hours
  2. distillationAfter distilling off 6 cm3 of an azeotrope of methanol and toluene
  3. washthe residue was washed with sodium carbonate solution
  4. customdried
  5. distillation18 g of 2-hexyloxythiophene of b.p. 66° C./0.26 mbar were distilled off

Sources & evidence

ORD record
ord-ae892ba445064f4d9cdaed52c1921818
Source dataset
uspto-grants-1990_06
Patent number
US04931568

Reaction notes

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