Methanol → Methyl 3-Hydroxyphenylacetate

HRID 906491Notes

Reaction equation

HRID 906491 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:12]O>S(=O)(=O)(O)O>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 39129Methyl 3-Hydroxyphenylacetate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

10 g of 3-hydroxyphenylacetic acid are dissolved in 60 ml of methanol and 2.5 ml of sulphuric acid. The solution is heated at reflux for two hours. It is brought back to ambient temperature and the methanol is evaporated. The residue is taken up in a saturated K2CO3 solution. Extraction is carried out with AcOEt. The organic phase is dried over MgSO4, filtered and evaporated to dryness. 11.1 g of oil are obtained.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for two hours
  3. customis brought back to ambient temperature
  4. customthe methanol is evaporated
  5. extractionExtraction
  6. dry with materialThe organic phase is dried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-93858637826f4c608dca446e7e3ecfd3
Source dataset
uspto-grants-2011_09
Patent number
US08012991B2

Reaction notes

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