p-Toluenesulfonic acid → Ethyl (3-Hydroxyphenyl)acetate

HRID 1872566Notes

Reaction equation

HRID 1872566 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:12]1(C)C=CC(S(O)(=O)=O)=C[CH:13]=1>C(O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 572437Ethyl (3-Hydroxyphenyl)acetateYield 893.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 3-hydroxyphenylacetic acid (5.4 g) and para-toluensulfonic acid (650 mg) in 80 ml of ethanol is refluxed for 4 hours, then the solvent is evaporated off and the residue is dissolved in ethyl acetate and washed twice with a saturated aqueous solution of sodium hydrogencarbonate. The organic phase is dried over sodium sulfate and the solvent is evaporated off to give 6.08 g of the product as a yellow oil.

Workup

  1. temperatureis refluxed for 4 hours
  2. customthe solvent is evaporated off
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed twice with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-afa9241f9fcd4f479db0f330a3fab2e9
Source dataset
uspto-grants-2000_08
Patent number
US06110924

Reaction notes

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