Benzaldehyde → 4,5-Dimethyl-2-Phenyl-1,3-Dithiolane

HRID 462575

Reaction equation

HRID 462575 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.C1CCCCC1.[CH3:18][CH:19]([SH:23])[CH:20]([SH:22])[CH3:21].C(=O)C1C=CC=CC=1>O>[CH3:21][CH:20]1[CH:19]([CH3:18])[S:23][CH:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:22]1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 8078CyclohexaneHCID 5483532,3-Butanedithiol

Product 1

HCID 203986774,5-Dimethyl-2-Phenyl-1,3-Dithiolane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 100 ml reaction flask equipped with thermometer, reflux condenser and magnetic stirring bar and hot plate with magnetic stirring apparatus is placed 0.5 grams of para-toluenesulfonic acid, 5.0 ml cyclohexane and 6.1 grams (0.05 moles) of 2,3-butanedithiol. Over a period of 25 minutes, 5.3 grams (0.05 moles) of benzaldehyde is added to the reaction mass with stirring. The reaction mass is then heated to reflux with stirring and refluxed for a period of 9.5 hours while taking off water of reaction. At the end of the refluxing period, the reaction mass is cooled to room temperature and transferred to a separatory funnel. The reaction mass is then washed with one 50 ml portion of saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and filtered. The resulting filtrate is distilled on a Microvigreux column yielding the following three fractions:

Workup

  1. customInto a 100 ml reaction flask
  2. customequipped with thermometer
  3. temperaturereflux condenser and magnetic stirring bar
  4. temperatureThe reaction mass is then heated
  5. temperatureto reflux
  6. stirringwith stirring
  7. temperaturerefluxed for a period of 9.5 hours
  8. customtransferred to a separatory funnel
  9. washThe reaction mass is then washed with one 50 ml portion of saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. distillationThe resulting filtrate is distilled on a Microvigreux column
  13. customyielding the following three fractions

Sources & evidence

ORD record
ord-677da6f870204dd18eaecd4cabad47c2
Source dataset
uspto-grants-1985_05
Patent number
US04515968

Linked notes

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