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

HRID 1981646Notes

Reaction equation

HRID 1981646 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-hyroxyphenylacetic acid in 500 mL methanol and 2 mL concentrated sulfuric acid was placed in a Soxhlet extractor charged with 3A 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. temperatureThe solution was heated
  2. temperatureto reflux for 72 hours
  3. waitthe sieves were exchanged at 24-hour
  4. customThe reaction medium was then evaporated to an oil which
  5. dissolutionwas dissolved in 100 mL toluene
  6. extractionextracted with 3×100 mL water
  7. dry with materialThe toluene phase was dried over magnesium sulfate
  8. additiontreated with activated charcoal
  9. customevaporated

Sources & evidence

ORD record
ord-76e128dc256a4f9d932836c3db209101
Source dataset
uspto-grants-1986_06
Patent number
US04593119

Reaction notes

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