Ethylene Glycol → 2-[2-(Methylsulfanyl)ethyl]-1,3-dioxolane

HRID 462569Notes

Reaction equation

HRID 462569 reaction equation
C1(C)[CH:6]=[CH:5][C:4]([S:7](O)(=O)=O)=CC=1.[CH2:12]([OH:15])[CH2:13][OH:14].[CH3:16]CCC=S>C1CCCCC1>[CH3:16][S:7][CH2:4][CH2:5][CH:6]1[O:15][CH2:12][CH2:13][O:14]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 12463483HCID 12463483, compound

Product 1

HCID 203986662-[2-(Methylsulfanyl)ethyl]-1,3-dioxolane

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 5 ml cyclohexane, 0.2 grams para-toluenesulfonic acid and 3.1 grams (0.05 moles) of 1,2-ethanediol. Over a period of 30 minutes, 5.2 grams (0.05 moles) of 3-methylthiopropionaldehyde is added to the reaction mass. The reaction mass is then heated to reflux and during reflux, water of formation is removed. The refluxing continues for a period of 9 hours. At the end of the 9 hour period, the reaction mass is cooled and transferred to a separatory funnel and washed with one 50 ml portion of saturated sodium chloride solution. The reaction mass is 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 then heated
  6. temperatureto reflux
  7. temperatureduring reflux
  8. customwater of formation is removed
  9. waitThe refluxing continues for a period of 9 hours
  10. temperatureAt the end of the 9 hour period, the reaction mass is cooled
  11. customtransferred to a separatory funnel
  12. washwashed with one 50 ml portion of saturated sodium chloride solution
  13. dry with materialThe reaction mass is then dried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. distillationdistilled on a Microvigreux column
  16. customyielding the following fractions

Sources & evidence

ORD record
ord-15e0e6d7877e4a7fb44a6ac360eda85b
Source dataset
uspto-grants-1985_05
Patent number
US04515966

Reaction notes

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