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

HRID 615930

Reaction equation

HRID 615930 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][CH:13]([SH:17])[CH:14]([SH:16])[CH3:15].[CH3:18][C:19](=[CH:21][CH2:22][CH2:23][C:24](=[CH:26][CH:27]=O)[CH3:25])[CH3:20]>C1CCCCC1>[CH3:25][C:24]([CH2:23][CH2:22][CH:21]=[C:19]([CH3:20])[CH3:18])=[CH:26][CH:27]1[S:17][CH:13]([CH3:12])[CH:14]([CH3:15])[S:16]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 88433,7-Dimethylocta-2,6-Dienal2×HCID 5483532,3-Butanedithiol

Product 1

HCID 545081782-(2,6-Dimethylhepta-1,5-dien-1-yl)-4,5-dimethyl-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 6.1 grams (0.05 moles) of 2,3-butanedithiol. Over a period of 30 minutes with stirring is added to the reaction mass 7.6 grams (0.05 moles) of citral having the structure: ##STR23## After the citral is added, the reaction mass is heated to reflux and refluxed (with removal of water of reaction) over a period of 9 hours. At the end of the 9 hour 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 and then dried over anhydrous sodium sulfate, filtered and 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
  8. custom(with removal of water of reaction) over a period of 9 hours
  9. temperatureAt the end of the 9 hour period, the reaction mass is cooled
  10. customtransferred to a separatory funnel
  11. washThe reaction mass is then washed with one 50 ml portion of saturated sodium chloride solution
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. distillationdistilled on a Microvigreux column
  15. customyielding the following fractions

Sources & evidence

ORD record
ord-bb530340671e4980a242fd11d183fa18
Source dataset
uspto-grants-1985_02
Patent number
US04501904

Linked notes

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