Reaktion #65734

Reaktionsgleichung

3-phenoxypropionic acid

p-toluenesulfonic acid

→

named product

Methyl 3-phenoxypropionate

Lösungsmittel

water

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux under nitrogen atmosphere in a 1 L round-bottom flask though 3 Å, 8-12 mesh molecular sieves which
2. 2
   Sonstigeis equipped with a soxhlet extractor and condenser
3. 3
   TemperaturThe mixture was heated
4. 4
   Temperaturat reflux for 21 hr
5. 5
   Temperaturcooled
6. 6
   SonstigeMethanol was removed on a rotary evaporator
7. 7
   Sonstigeto leave a light yellow oil which
8. 8
   Extraktionextracted with ether (3×75 mL)
9. 9
   WaschenThe combined ether extracts were washed with NaHCO3 solution, water and brine
10. 10
    Trocknendried over MgSO4
11. 11
    SonstigeRemoval of the solvent
12. 12
    workup.DISTILLATIONKugelrohr distillation (80° C., 0.8 mm Hg)

Vorschrift

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.

Quelle