Methanol → Methyl 3-Hydroxyphenylacetate

HRID 37129

Reaction equation

HRID 37129 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.OS(O)(=O)=O.[CH3:17]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:17])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 39129Methyl 3-HydroxyphenylacetateYield 71%

Procedure

To a solution of 3-hydroxyphenylacetic acid (2 g, 13.2 mmol) in methanol (45 mL) was added concentrated H2SO4 (0.82 mL) and the mixture was heated at reflux for 18 h. Next, the solvent was removed and the residue was diluted with water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed, to yield 1.54 g of the desired compound (yield: 71%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 h
  3. customNext, the solvent was removed
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-bf58182e499b4b8590ee23072ae2a58a
Source dataset
uspto-grants-1995_05
Patent number
US05420131

Linked notes

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