p-Toluenesulfonic acid → Methyl 3-phenoxypropionate

Participants

Reaction Steps

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.

Provenance & Evidence