p-Toluenesulfonic acid → Ethyl 2-(4-phenoxyphenyl)acetate

HRID 993078Notes

Reaction equation

HRID 993078 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1(C)C=CC(S(O)(=O)=O)=C[CH:19]=1>C(O)C>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 2390774-Phenoxyphenylacetic acid

Product 1

HCID 13567666Ethyl 2-(4-phenoxyphenyl)acetateYield 404.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of (4′-phenoxyphenyl)acetic acid (0.456 g) in 4 ml of ethanol is added para-toluensulfonic acid (0.076 g) and the resulting mixture is refluxed for 2 hours. The solvent is evaporated off, the residue is dissolved in diethyl ether and the organic phase is washed with saturated aqueous solution of sodium hydrogencarbonate and then with brine. The organic phase is dried over sodium sulfate and concentrated to dryness to give 0.458 g of the product as a brown oil.

Workup

  1. temperaturethe resulting mixture is refluxed for 2 hours
  2. customThe solvent is evaporated off
  3. dissolutionthe residue is dissolved in diethyl ether
  4. washthe organic phase is washed with saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9aa64fa48516403c9996634f5814ee5f
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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