p-Toluenesulfonic acid → 4-Methyl-2-[2-(methylsulfanyl)ethyl]-1,3-dioxane

HRID 462570Notes

Reaction equation

HRID 462570 reaction equation
C1(C)C=C[C:4]([S:7](O)(=O)=O)=[CH:3][CH:2]=1.[CH2:12]1CCCCC1.[CH2:18]([OH:23])[CH2:19][CH:20]([OH:22])[CH3:21].CCCC=S>O>[CH3:21][CH:20]1[CH2:19][CH2:18][O:23][CH:2]([CH2:3][CH2:4][S:7][CH3:12])[O:22]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 78961,3-ButanediolHCID 8078CyclohexaneHCID 12463483Butanthial

Product 1

HCID 203986644-Methyl-2-[2-(methylsulfanyl)ethyl]-1,3-dioxane

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 0.2 grams para-toluenesulfonic acid, 5 ml cyclohexane and 4.5 grams of 1,3-butanediol. Slowly added to the reaction mass over a period of 30 minutes is 3-methylthiopropionaldehyde (5.2 grams; 0.05 moles). The reaction mass is then heated to reflux and refluxed for a period of 9 hours. During the refluxing process, water of reaction is removed from the reaction mass. At the end of the 9 hour refluxing period, the reaction mass is then cooled and transferred to a separatory funnel and 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. additionSlowly added to the reaction mass over a period of 30 minutes
  6. temperatureThe reaction mass is then heated
  7. temperatureto reflux
  8. temperaturerefluxed for a period of 9 hours
  9. customis removed from the reaction mass
  10. temperatureAt the end of the 9 hour refluxing period
  11. temperaturethe reaction mass is then cooled
  12. customtransferred to a separatory funnel
  13. washwashed with one 50 ml portion of saturated sodium chloride solution
  14. dry with materialdried over anhydrous sodium sulfate
  15. filtrationfiltered
  16. distillationdistilled on a Microvigreux column
  17. customyielding the following fractions

Sources & evidence

ORD record
ord-45178722cb6b401a9f3c6a4bb09a6d0c
Source dataset
uspto-grants-1985_05
Patent number
US04515966

Reaction notes

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