p-Toluenesulfonic acid → Cyclopentyl-2-mercaptopropionate

HRID 280502Notes

Reaction equation

HRID 280502 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[SH:7][CH:8]([CH3:12])[C:9](O)=[O:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C>[CH:1]1([O:6][C:9](=[O:10])[CH:8]([SH:7])[CH3:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7298CyclopentanolHCID 62326(+-)-2-Mercaptopropionic acid

Product 1

HCID 20212356Cyclopentyl-2-mercaptopropionate

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 86 grams of cyclopentanol; 25 grams of 2-mercaptopropionic acid; and 1 gram of paratoluene sulfonic acid. The reaction mass is heated to reflux and refluxed for a period of 8 hours. At the end of the 8 hour reflux period, the reaction mass is cooled and admixed with 200 ml diethylether followed by washing with two 100 ml volumes of 10% aqueous sodium carbonate and one 100 ml volume of water. The reaction mass is dried over anhydrous sodium sulfate and the solvent is recovered on a Buchi apparatus. The reaction mass is then micro distilled yielding the product having the structure: ##STR135##

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 8 hours
  8. temperatureAt the end of the 8 hour reflux period
  9. temperaturethe reaction mass is cooled
  10. washby washing with two 100 ml volumes of 10% aqueous sodium carbonate and one 100 ml volume of water
  11. dry with materialThe reaction mass is dried over anhydrous sodium sulfate
  12. customthe solvent is recovered on a Buchi apparatus
  13. distillationThe reaction mass is then micro distilled
  14. customyielding the product

Sources & evidence

ORD record
ord-93cdd480d674440988e5eabc8dc6d7cb
Source dataset
uspto-grants-1986_05
Patent number
US04590082

Reaction notes

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