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

HRID 615931

Reaction equation

HRID 615931 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-580f0a123d7049b5a0d79aeac2043eb8
Source dataset
uspto-grants-1985_02
Patent number
US04501904

Linked notes

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