Methanol → Methyl 3-Hydroxyphenylacetate

HRID 902688Notes

Reaction equation

HRID 902688 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>>[CH3:17][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 39129Methyl 3-HydroxyphenylacetateYield 99%

Procedure

To a stirring solution of (3-hydroxy-phenyl)-acetic acid (4.3 g, 0.028 mole) in methanol (30 mL) was added H2SO4 (1 mL) and the mixture was heated to reflux for 2 hours. The solvent was removed, the residue was washed with H2O, and extracted three times with EtOAc (ethyl acetate). The combined organic layers were dried over Na2SO4, filtered, and concentrated to give 4.7 g (99% yield) of the title compound as an oil. MS (ESI) 167.0(M+H+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed
  4. washthe residue was washed with H2O
  5. extractionextracted three times with EtOAc (ethyl acetate)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ac0ce07e2e154b1d82985c131df321bd
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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