Cyclohexane → 4,5-Dimethyl-2-[2-(methylsulfanyl)ethyl]-1,3-oxathiolane

HRID 462566Notes

Reaction equation

HRID 462566 reaction equation
[CH2:1]1[CH2:6]CCC[CH2:2]1.[SH:7][CH:8]([CH3:12])[CH:9]([OH:11])[CH3:10].CCC[CH:16]=[S:17]>O>[CH3:12][CH:8]1[CH:9]([CH3:10])[O:11][CH:2]([CH2:1][CH2:6][S:17][CH3:16])[S:7]1

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 620872-Mercapto-3-butanolHCID 12463483HCID 12463483, compound

Product 1

HCID 203986674,5-Dimethyl-2-[2-(methylsulfanyl)ethyl]-1,3-oxathiolane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 100 ml reaction flask equipped with spin bar, reflux condenser, heating mantle, hot plate apparatus (with magnetic stirring apparatus) is placed 5 ml cyclohexane, 0.2 grams paratoluenesulfonic acid and 5.3 grams (0.05 moles) of 3-mercapto-2-butanol. Over a period of 30 minutes, 5.2 grams (0.05 moles) of 3-methylthiopropionaldehyde are added to the reaction mass. The reaction mass is then heated to reflux and water of reaction is continuously removed during the refluxing of the reaction mass. The reaction takes place over a period of 7 hours. At the end of the 7 hours the reaction mass is transferred to a separatory funnel and the reaction mass is washed with one 50 ml portion of saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The product is then 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 then heated
  6. temperatureto reflux
  7. customis continuously removed during the
  8. temperaturerefluxing of the reaction mass
  9. customof 7 hours
  10. customAt the end of the 7 hours the reaction mass is transferred to a separatory funnel
  11. washthe reaction mass is washed with one 50 ml portion of saturated aqueous sodium chloride solution
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationThe product is then filtered
  14. distillationdistilled on a Microvigreux column
  15. customyielding the following fractions

Sources & evidence

ORD record
ord-47f1e58a12d94fbf9d97db139d04339c
Source dataset
uspto-grants-1985_05
Patent number
US04515966

Reaction notes

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