p-Toluenesulfonic acid → Felbinac ethyl

HRID 993076Notes

Reaction equation

HRID 993076 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O-:16])=[O:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1(C)C=CC(S(O)(=O)=O)=C[CH:18]=1>C(O)C>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 6919042HCID 6919042, compound

Product 1

HCID 26436Felbinac ethylYield 462.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of (4′-biphenyl)acetate acid (6.4 g) in 60 ml of ethanol is added with 1.1 g of para-toluensulfonic acid, then the reaction mixture is refluxed for 4 hours 30 minutes. The solvent is evaporated off, the residue is dissolved in diethyl ether and the resulting organic phase is washed three times with a saturated aqueous solution of sodium hydrogencarbonate and once with brine. The organic phase is then dried over sodium sulfate and the solvent is evaporated off to give 7.1 g of the product as a yellow oil.

Workup

  1. temperaturethe reaction mixture is refluxed for 4 hours 30 minutes
  2. customThe solvent is evaporated off
  3. dissolutionthe residue is dissolved in diethyl ether
  4. washthe resulting organic phase is washed three times with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialThe organic phase is then dried over sodium sulfate
  6. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-6444000fbe67474f8565ec27e7afdf8f
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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