HCID 20297259, compound → Fenoprofen

HRID 1389622Notes

Reaction equation

HRID 1389622 reaction equation
C1(S[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)([CH3:12])[C:9]([OH:11])=[O:10])C=CC=CC=1>C(O)(=O)C.[Zn]>[O:19]([C:15]1[CH:14]=[C:13]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:18]=[CH:17][CH:16]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 20297259HCID 20297259, compound

Product 1

HCID 3342FenoprofenYield 95.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

1.11 g (3.17 mmols) of 2-phenylthio-2-(3-phenoxyphenyl)propionic acid obtained in Example 6 was dissolved in 10 ml of acetic acid and the solution was heated while refluxing for 1 hour with stirring in the presence of 1.0 g of zinc powder. The solid substance present in the reaction mixture was removed by filtration and washed with methylene chloride. The combined filtrate and washing was concentrated to obtain 0.86 g of a crude product which was then purified by silica gel column chromatography eluting with diethyl etherhexane (1:5 by volume) to obtain 0.73 g (95% yield) of 2-(3-phenoxyphenyl)propionic acid. nD26 1.5780.

Workup

  1. temperaturethe solution was heated
  2. temperaturewhile refluxing for 1 hour
  3. customThe solid substance present in the reaction mixture was removed by filtration
  4. washwashed with methylene chloride
  5. washThe combined filtrate and washing
  6. concentrationwas concentrated
  7. customto obtain 0.86 g of a crude product which
  8. customwas then purified by silica gel column chromatography
  9. washeluting with diethyl etherhexane (1:5 by volume)

Sources & evidence

ORD record
ord-78d64800a8f84abea13d5d20f977f0b7
Source dataset
uspto-grants-1981_01
Patent number
US04245108

Reaction notes

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