p-Toluenesulfonic acid → Cyclohexyl 3-sulfanylpropanoate

HRID 280503Notes

Reaction equation

HRID 280503 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[SH:8][CH2:9][CH2:10][C:11](O)=[O:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C>[CH:1]1([O:7][C:11](=[O:12])[CH2:10][CH2:9][SH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 65143-Mercaptopropionic AcidHCID 7966Cyclohexanol

Product 1

HCID 13651838Cyclohexyl 3-sulfanylpropanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a 250 ml reaction flask equipped with stirrer, thermometer, reflux condenser and heating mantle are placed 100 grams of cyclohexanol; 26 grams of 3-mercaptopropionic acid and 0.5 grams of paratoluene sulfonic acid. The reaction mass is heated to reflux and refluxed for a period of 11 hours. At the end of the 11 hour period of refluxing, the reaction mass is cooled to room temperature. 200 ml Diethylether are added to the reaction mass. The reaction mass is then washed with two 100 ml volumes of 10% aqueous sodium bicarbonate solution followed by one 100 ml volume of water. The reaction mass is dried over anhydrous sodium sulfate and the solvent is recovered on a Buchi evaportor. The reaction mass is then micro distilled on a micro distillation apparatus yielding the following fractions:

Workup

  1. customInto a 250 ml reaction flask
  2. customequipped with stirrer
  3. temperaturethermometer, reflux condenser
  4. temperatureheating mantle
  5. temperatureThe reaction mass is heated
  6. temperatureto reflux
  7. temperaturerefluxed for a period of 11 hours
  8. temperatureAt the end of the 11 hour period of refluxing
  9. washThe reaction mass is then washed with two 100 ml volumes of 10% aqueous sodium bicarbonate solution
  10. dry with materialThe reaction mass is dried over anhydrous sodium sulfate
  11. customthe solvent is recovered on a Buchi evaportor
  12. distillationThe reaction mass is then micro distilled on a micro distillation apparatus
  13. customyielding the following fractions

Sources & evidence

ORD record
ord-fbb8db47f2114ff093fcc83db450cbfd
Source dataset
uspto-grants-1986_05
Patent number
US04590082

Reaction notes

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