p-Toluenesulfonic acid → Phenylpropyl-2-mercaptopropionate

HRID 256233Notes

Reaction equation

HRID 256233 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SH:11][CH:12]([CH3:16])[C:13]([O-])=[O:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:1]1([CH2:7][CH2:8][CH2:9][O:10][C:13](=[O:14])[CH:12]([SH:11])[CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31234BenzenepropanolHCID 156077362-Mercaptopropionate

Product 1

HCID 54527705Phenylpropyl-2-mercaptopropionate

Procedure

Into a 100 ml reaction flask equipped with reflux condenser, hot plate (with stirring apparatus contained within) and spin bar are placed 13.6 grams phenylpropyl alcohol; 4.0 grams of 2-mercaptopropionate acid; and 0.1 grams of para-toluene sulphonic acid. The reaction mass is maintained at reflux for a period of 9 hours with stirring. At the end of the 9 hour period, the reaction mass is cooled and fractionally distilled on a micro distillation apparatus yielding the compound having the structure: ##STR64## (as confirmed by GLC, mass spectral, NMR and IR analyses).

Workup

  1. customInto a 100 ml reaction flask
  2. customequipped
  3. temperaturewith reflux condenser
  4. temperatureThe reaction mass is maintained
  5. temperatureat reflux for a period of 9 hours
  6. stirringwith stirring
  7. temperatureAt the end of the 9 hour period, the reaction mass is cooled
  8. distillationfractionally distilled on a micro distillation apparatus
  9. customyielding the compound

Sources & evidence

ORD record
ord-6b5dd6177a6445a88c5c34468dfc3e06
Source dataset
uspto-grants-1987_10
Patent number
US04701548

Reaction notes

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