p-Toluenesulfonic acid → Cyclooctyl-2-mercaptopropionate

HRID 280496Notes

Reaction equation

HRID 280496 reaction equation
[CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[SH:10][CH:11]([CH3:15])[C:12](O)=[O:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH:1]1([O:9][C:12](=[O:13])[CH:11]([SH:10])[CH3:15])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12766CyclooctanolHCID 62326(+-)-2-Mercaptopropionic acid

Product 1

HCID 20212357Cyclooctyl-2-mercaptopropionate

Procedure

Into a 100 ml reaction flask equipped with reflux condenser, thermometer, hot plate, spin bar and heating mantle are placed 12.8 grams of cyclooctanol; 22 grams of 2-mercaptopropionic acid and 0.5 grams of paratoluene sulfonic acid. The reaction mass is heated to reflux and maintained at reflux for a period of 10 hours. At the end of the reaction mass, the reaction product is washed with one 25 ml volume of water and dried over anhydrous sodium sulfate. The reaction mass is then distilled on a micro distillation column yielding the compound having the structure: ##STR99##

Workup

  1. customInto a 100 ml reaction flask
  2. customequipped
  3. temperaturewith reflux condenser
  4. temperatureheating mantle
  5. temperatureThe reaction mass is heated
  6. temperatureto reflux
  7. temperaturemaintained
  8. temperatureat reflux for a period of 10 hours
  9. washAt the end of the reaction mass, the reaction product is washed with one 25 ml volume of water
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe reaction mass is then distilled on a micro distillation column
  12. customyielding the compound

Sources & evidence

ORD record
ord-26ea7c941801438d9c5b1cc75dbd806c
Source dataset
uspto-grants-1986_05
Patent number
US04590082

Reaction notes

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