p-Toluenesulfonic acid → HCID 14178040, compound

HRID 649345Notes

Reaction equation

HRID 649345 reaction equation
[SH:1][CH:2]([CH3:6])[C:3]([OH:5])=[O:4].[CH2:7]([OH:10])[CH:8]=[CH2:9].[C:11]1(C)[CH:16]=CC(S(O)(=O)=O)=C[CH:12]=1>>[OH:10][CH2:7][CH2:8][CH2:9][S:1][CH:2]([CH3:6])[C:3]([O:5][CH2:16][CH:11]=[CH2:12])=[O:4]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7858Allyl AlcoholHCID 62326(+-)-2-Mercaptopropionic acid

Product 1

HCID 14178040HCID 14178040, compound

Procedure

Into a 250 cc reaction flask equipped with stirrer, thermometer, reflux condenser and heating mantle are placed 26.5 grams of 2-mercapto propionic acid (0.25 moles); 58 grams allyl alcohol (1.0 moles) and 0.2 grams of para-toluene sulfonic acid. With stirring, the reaction mass is heated to reflux and maintained at reflux for a period of 8 hours. At the end of the 8 hour period, the reaction mass is cooled to room temperature and transferred to a separatory funnel. The reaction mass is then extracted with two 250 ml portions of methylene dichloride. The methylene dichloride extracts are combined and washed with one 100 ml portion of saturated sodium carbonate solution followed by one 100 ml portion of saturated sodium chloride solution. The resulting organic material is dried over anhydrous sodium sulfate, filtered and distilled on a micro Vigreux column yielding the following fractions:

Workup

  1. customInto a 250 cc reaction flask
  2. customequipped with stirrer
  3. temperaturethermometer, reflux condenser
  4. temperatureheating mantle
  5. temperaturethe reaction mass is heated
  6. temperatureto reflux
  7. temperaturemaintained
  8. temperatureat reflux for a period of 8 hours
  9. customtransferred to a separatory funnel
  10. extractionThe reaction mass is then extracted with two 250 ml portions of methylene dichloride
  11. washwashed with one 100 ml portion of saturated sodium carbonate solution
  12. dry with materialThe resulting organic material is dried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. distillationdistilled on a micro Vigreux column
  15. customyielding the following fractions

Sources & evidence

ORD record
ord-29de19f8d7a94ed79b6e9f2f58e7778b
Source dataset
uspto-grants-1988_04
Patent number
US04739105

Reaction notes

Loading…