Acetic Acid → Fenoprofen

Participants

Reaction Steps

The oil from Example 27, 1,1-dimethoxy-1-(3-phenoxyphenyl)prop-2-yl methanesulfonate, and 14.9 g of sodium acetate are dissolved in 200 ml of acetic acid and the resulting mixture is heated to reflux. After refluxing for four hours, the mixture is cooled to 25° C. and most of the acetic acid is removed by distillation. The residue is dissolved in 150 ml of ethyl ether and extracted several times with water. The ether is evaporated and replaced by 10 ml of methanol, 50 ml of water, and 7.5 g of sodium hydroxide. The resulting mixture is heated to reflux and refluxed for one hour. The methanol is removed by distillation and the resulting aqueous solution is extracted with 200 ml methylene chloride and acidified with hydrochloric acid. The suspension formed is extracted with 150 ml of methylene chloride and the organic layer is dried over magnesium sulfate. The solvent is removed to yield 4.04 g of 2-(3-phenoxyphenyl)propionic acid [which is characterized by an NMR spectra in deuterochloroform of τ =8.54 (doublet, J=2.5), 5.23 (quartet, J=2.5), 2.45-3.15 (multiplet), 1.5.]

Provenance & Evidence