Acetic Acid → Fenoprofen

HRID 1907020Notes

Reaction equation

HRID 1907020 reaction equation
CS(OC(C)C(OC)(OC)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)(=O)=O.[C:26]([O-:29])(=[O:28])[CH3:27].[Na+].[C:31](O)(=O)C>>[O:14]([C:15]1[CH:20]=[C:19]([CH:27]([CH3:31])[C:26]([OH:29])=[O:28])[CH:18]=[CH:17][CH:16]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 517045Sodium AcetateHCID 20211455HCID 20211455, compound2×

Product 1

HCID 3342Fenoprofen

Procedure

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.]

Workup

  1. temperaturethe resulting mixture is heated to reflux
  2. temperatureAfter refluxing for four hours
  3. customis removed by distillation
  4. dissolutionThe residue is dissolved in 150 ml of ethyl ether
  5. extractionextracted several times with water
  6. customThe ether is evaporated
  7. temperatureThe resulting mixture is heated
  8. temperatureto reflux
  9. temperaturerefluxed for one hour
  10. customThe methanol is removed by distillation
  11. extractionthe resulting aqueous solution is extracted with 200 ml methylene chloride
  12. customThe suspension formed
  13. extractionis extracted with 150 ml of methylene chloride
  14. dry with materialthe organic layer is dried over magnesium sulfate
  15. customThe solvent is removed

Sources & evidence

ORD record
ord-f584b5e13eaf4239b94f253676cb0611
Source dataset
uspto-grants-1987_03
Patent number
US04654438

Reaction notes

Loading…