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

HRID 2166516Notes

Reaction equation

HRID 2166516 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.[CH3:12]O>S(=O)(=O)(O)O>[CH3:12][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 127Hydroxyphenylacetic acidHCID 887Methanol

Product 1

HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 15 gm (0.1 mole) of 4-hydroxyphenylacetic acid in 500 mL methanol and 2 mL concentrated sulfuric acid was placed in a Soxhlet extractor charged with 3 A molecular sieves. The solution was heated to reflux for 72 hours, and the sieves were exchanged at 24-hour intervals. The reaction medium was then evaporated to an oil which was dissolved in 100 mL toluene and extracted with 3×100 mL water. The toluene phase was dried over magnesium sulfate, treated with activated charcoal and evaporated to provide 13 gm (80% yield) of a yellow oil. The NMR spectrum was consistent with the assigned structure and this material was used in the next reaction step.

Workup

  1. additioncharged with 3 A molecular sieves
  2. temperatureThe solution was heated
  3. temperatureto reflux for 72 hours
  4. waitthe sieves were exchanged at 24-hour
  5. customThe reaction medium was then evaporated to an oil which
  6. dissolutionwas dissolved in 100 mL toluene
  7. extractionextracted with 3×100 mL water
  8. dry with materialThe toluene phase was dried over magnesium sulfate
  9. additiontreated with activated charcoal
  10. customevaporated

Sources & evidence

ORD record
ord-8b1d8aefb8154adf80b4356eb853ccfc
Source dataset
uspto-grants-1983_06
Patent number
US04387103

Reaction notes

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