p-Toluenesulfonic acid → Methyl 3-phenoxypropionate

HRID 37456

Reaction equation

HRID 37456 reaction equation
[O:1]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O>[O:1]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 815963-Phenoxypropionic acid

Product 1

HCID 347927Methyl 3-phenoxypropionateYield 2,255.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-phenoxypropionic acid (25 g, 150.4 mmol) and p-toluenesulfonic acid (1.23 g, 6.46 mmol) in 500 mL of methanol was heated to reflux under nitrogen atmosphere in a 1 L round-bottom flask though 3 Å, 8-12 mesh molecular sieves which is equipped with a soxhlet extractor and condenser. The mixture was heated at reflux for 21 hr and then cooled. Methanol was removed on a rotary evaporator to leave a light yellow oil which was taken up in 50 mL of water and then extracted with ether (3×75 mL). The combined ether extracts were washed with NaHCO3 solution, water and brine and dried over MgSO4. Removal of the solvent and then Kugelrohr distillation (80° C., 0.8 mm Hg) gave a yield of 26.26 g (97%) of the named product.

Workup

  1. temperatureto reflux under nitrogen atmosphere in a 1 L round-bottom flask though 3 Å, 8-12 mesh molecular sieves which
  2. customis equipped with a soxhlet extractor and condenser
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 21 hr
  5. temperaturecooled
  6. customMethanol was removed on a rotary evaporator
  7. customto leave a light yellow oil which
  8. extractionextracted with ether (3×75 mL)
  9. washThe combined ether extracts were washed with NaHCO3 solution, water and brine
  10. dry with materialdried over MgSO4
  11. customRemoval of the solvent
  12. distillationKugelrohr distillation (80° C., 0.8 mm Hg)

Sources & evidence

ORD record
ord-8e163dc07caa4386ba96a1ef46caa7fe
Source dataset
uspto-grants-1995_05
Patent number
US05420295

Linked notes

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