p-Toluenesulfonic acid → 2-(2,6-Dimethylhepta-1,5-dien-1-YL)-4-methyl-1,3-dithiolane

HRID 358111

Reaktionsgleichung

Reaktionsgleichung von HRID 358111
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([SH:16])[CH:13]([SH:15])[CH3:14].[CH3:17][C:18](=[CH:20][CH2:21][CH2:22][C:23](=[CH:25][CH:26]=O)[CH3:24])[CH3:19]>C1CCCCC1>[CH3:24][C:23]([CH2:22][CH2:21][CH:20]=[C:18]([CH3:19])[CH3:17])=[CH:25][CH:26]1[S:15][CH:13]([CH3:14])[CH2:12][S:16]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 88433,7-Dimethylocta-2,6-Dienal2×HCID 612172,3-Dimercaptopropane

Produkt 1

HCID 537097522-(2,6-Dimethylhepta-1,5-dien-1-YL)-4-methyl-1,3-dithiolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

Into a 100 ml reaction flask equipped with spin bar, reflux condenser, heating mantle and hot plate with magnetic stirring apparatus is placed 0.5 grams para-toluenesulfonic acid, 5.0 ml cyclohexane and 5.4 grams (0.05 moles) of 1,2-propanedithiol. 7.6 grams (0.05 moles) of citral is then added to the reaction mass over a period of 30 minutes. After the addition of the citral, the reaction mass is heated to reflux and refluxed for a period of 10 hours while removing water of reaction. After the 10 hour reflux period, the reaction mass is cooled and transferred to a separatory funnel. The reaction mass is then washed with one 50 ml portion of saturated sodium chloride solution followed by drying over anhydrous sodium sulfate and filtration. The resulting filtrate is distilled on a Microvigreux column yielding the following fractions:

Aufarbeitung

  1. customInto a 100 ml reaction flask
  2. customequipped with spin bar
  3. temperaturereflux condenser
  4. temperatureheating mantle
  5. temperaturethe reaction mass is heated
  6. temperatureto reflux
  7. temperaturerefluxed for a period of 10 hours
  8. customwhile removing
  9. customwater of reaction
  10. temperatureAfter the 10 hour reflux period
  11. temperaturethe reaction mass is cooled
  12. customtransferred to a separatory funnel
  13. washThe reaction mass is then washed with one 50 ml portion of saturated sodium chloride solution
  14. dry with materialby drying over anhydrous sodium sulfate and filtration
  15. distillationThe resulting filtrate is distilled on a Microvigreux column
  16. customyielding the following fractions

Quellen und Nachweise

ORD-Eintrag
ord-c103b1f90a7442be894cd32749f239a5
Quelldatensatz
uspto-grants-1984_08
Patentnummer
US04464408

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