p-Toluenesulfonic acid → Ethyl 4-methoxyphenylacetate

HRID 1872552Notes

Reaction equation

HRID 1872552 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[C:13]1(C)C=CC(S(O)(=O)=O)=C[CH:14]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 76904-Methoxyphenylacetic Acid

Product 1

HCID 84174Ethyl 4-methoxyphenylacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-methoxyphenylacetic acid (2 g) and para-toluensulfonic acid (230 mg) in 30 ml of ethanol is refluxed for 2 hours. The solvent is evaporated under reduced pressure and the residue is suspended in a saturated aqueous solution of sodium hydrogencarbonate and extracted twice with ethyl acetate. The organic extracts are collected, washed with water and dried over sodium sulfate to give, after evaporation of the solvent under reduced pressure, 2.14 g of the product.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. extractionextracted twice with ethyl acetate
  3. customThe organic extracts are collected
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customto give
  7. customafter evaporation of the solvent under reduced pressure, 2.14 g of the product

Sources & evidence

ORD record
ord-658ff7183a0e4eeb860f6066d47f4b9d
Source dataset
uspto-grants-2000_08
Patent number
US06110924

Reaction notes

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