Hexanal → 3-Methoxy-4-hexyloxythiophene

HRID 2106901Notes

Reaction equation

HRID 2106901 reaction equation
[CH3:1][O:2][C:3]1[C:7]([O:8][CH3:9])=[CH:6][S:5][CH:4]=1.OS([O-])(=O)=O.[Na+].[CH:16](=O)[CH2:17][CH2:18][CH2:19][CH2:20]C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:7]([O:8][CH2:9][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:6][S:5][CH:4]=1

Participants

5

Reactant 3

HCID 6184HexanalHCID 516919Sodium BisulfateHCID 36135013,4-Dimethoxythiophene

Product 1

HCID 144732273-Methoxy-4-hexyloxythiophene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 g of 3,4-dimethoxythiophene were dissolved in 10 cm3 of 1-hexanone and 30 cm3 of toluene, 0.5 g of NaHSO4 was added, and the mixture was heated to reflux. 6 cm3 of azeotrope were distilled off and the batch was then worked up as in Example 14. Fractionation gave 3.7 g of 3-methoxy-4-hexyloxythiophene, b.p. 80° to 85° C./0.1 mbar. 4 g of dihexyloxythiophene were obtained from the distillation residue by chromatography through SiO2 using CH2Cl2.

Workup

  1. temperaturethe mixture was heated to reflux
  2. distillation6 cm3 of azeotrope were distilled off

Sources & evidence

ORD record
ord-e4311e58362e4be389a2213e1d0632f2
Source dataset
uspto-grants-1990_06
Patent number
US04931568

Reaction notes

Loading…