Reaktion #95553

Reaktionsgleichung

NaI

6,6-dimethoxy-1-hexanal

p-toluene-sulfonyl chloride

pyridine

→

1,1-dimethoxy-6-iodohexane

Ausbeute 92.0%

Lösungsmittel

water

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   Sonstigeremained below 15°
3. 3
   Extraktionthe mixture was extracted with ether
4. 4
   WaschenThe organic layer was washed with 5% aq. AcOH, cold 2% NaOH
5. 5
   Trocknendried (Na2SO4)
6. 6
   Sonstigeevaporated at 20°
7. 7
   workup.DISSOLUTIONThe residue (190 g) was dissolved in 500 ml of acetone
8. 8
   workup.STIRRINGthe mixture was stirred for 24 h at room temperature
9. 9
   SonstigeMost of the solvent was removed in vacuo
10. 10
    workup.ADDITIONether was added
11. 11
    WaschenThe mixture was washed with water
12. 12
    Trocknendried (Na2SO4)
13. 13
    Sonstigeevaporated
14. 14
    workup.DISTILLATIONdistilled

Vorschrift

81 g (0.5 Mole) of 6,6-dimethoxy-1-hexanal was added to an ice-cooled mixture of 99.3 g (0.52 Mole) of p-toluene-sulfonyl chloride and 72 ml (0.9 Mole) of pyridine at such a rate that the temperature remained below 15°. Stirring was continued for 2 h at 5°-10°, then cold water was added and the mixture was extracted with ether. The organic layer was washed with 5% aq. AcOH, cold 2% NaOH, dried (Na2SO4), and evaporated at 20°. The residue (190 g) was dissolved in 500 ml of acetone, then a solution of 97.5 g (0.65 Mole) of NaI in 500 ml of acetone was added, and the mixture was stirred for 24 h at room temperature. Most of the solvent was removed in vacuo, then ether was added. The mixture was washed with water, dried (Na2SO4), evaporated and distilled to give 124.9 g (92%) of 1,1-dimethoxy-6-iodohexane, b.p. 76°-78°/0.05 Torr.

Quelle