Hydroxyphenylacetic acid → Benzeneacetic acid, 4-hydroxy-, methyl ester

HRID 441202Notes

Reaction equation

HRID 441202 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12]1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 127Hydroxyphenylacetic acidHCID 6101p-Toluenesulfonic acid

Product 1

HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxyphenylacetic acid (10 g) in methylene chloride (66 mL) and methanol (26 mL) was added p-toluenesulfonic acid (1.25 g), and the resulting solution was heated at reflux overnight. The solvent was evaporated, the residue dissolved in ethyl acetate, and the the solution washed (H2O), dried (MgSO4), and evaporated to give crude methyl 4-hydroxyphenylacetate (10.4 TLC: Rf =0.72, ethyl acetate:dichloromethane (10:90); MS: m/z=167(M+1).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washthe the solution washed (H2O)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-c706623709e64702a023512a40552bfb
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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