Methanol → Methyl (2-hydroxyphenyl)acetate

HRID 1731769Notes

Reaction equation

HRID 1731769 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 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 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. 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 portions of water
  8. dry with materialThe toluene phase was dried over magnesium sulfate
  9. additiontreated with activated charcoal
  10. customevaporated

Sources & evidence

ORD record
ord-50b597f0cca142ab97fb150bd7b50e94
Source dataset
uspto-grants-1986_11
Patent number
US04623652

Reaction notes

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