Propylene Glycol → 1,3-Dioxolane, 4-methyl-2-[2-(methylthio)ethyl]-

HRID 462568Notes

Reaction equation

HRID 462568 reaction equation
[CH2:1]1[CH2:6][CH2:5]CCC1.C1(C)C=C[C:10]([S:13](O)(=O)=O)=CC=1.[CH2:18]([OH:22])[CH:19]([OH:21])[CH3:20].CCCC=S>O>[CH3:20][CH:19]1[CH2:18][O:22][CH:1]([CH2:6][CH2:5][S:13][CH3:10])[O:21]1

Participants

6

Reactant 4

HCID 1030Propylene GlycolHCID 6101p-Toluenesulfonic acidHCID 8078CyclohexaneHCID 12463483Butanthial

Product 1

HCID 1009271,3-Dioxolane, 4-methyl-2-[2-(methylthio)ethyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 3.8 grams (0.05 moles) of 1,2-propanediol. Over a period of 8 hours, 3-methylthiopropionaldehyde is added to the reaction mass. The reaction mass is then heated to reflux and during refluxing water of formation is removed. The refluxing continues for a period of 7 hours. At the end of the 7 hour period, the reaction mass is transferred to a separatory funnel and washed with one 50 ml portion of saturated aqueous 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 then heated
  6. temperatureto reflux
  7. customis removed
  8. waitThe refluxing continues for a period of 7 hours
  9. customAt the end of the 7 hour period, the reaction mass is transferred to a separatory funnel
  10. washwashed with one 50 ml portion of saturated aqueous sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. distillationdistilled on a Microvigreux column
  14. customyielding the following fractions

Sources & evidence

ORD record
ord-dee058d289184193a15c03ac9d87f9af
Source dataset
uspto-grants-1985_05
Patent number
US04515966

Reaction notes

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