Methanol → Methyl (2-hydroxyphenyl)acetate

HRID 1164996Notes

Reaction equation

HRID 1164996 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[CH3:12]O>S(=O)(=O)(O)O>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 887MethanolHCID 11970(2-Hydroxyphenyl)acetic acid

Product 1

HCID 89719Methyl (2-hydroxyphenyl)acetateYield 80%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 15 gm (0.1 mole) of 2-hydroxyphenylacetic 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 tolene and extracted with 3×100 ml portions of 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 tolene
  6. extractionextracted with 3×100 ml portions of water
  7. dry with materialThe toluene phase was dried over magnesium sulfate
  8. additiontreated with activated charcoal
  9. customevaporated

Sources & evidence

ORD record
ord-5cf8c309cce84f0b866fb7af4257c2cd
Source dataset
uspto-grants-1990_03
Patent number
US04906661

Reaction notes

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