Methanol → Methyl 3-Hydroxyphenylacetate

HRID 854536Notes

Reaction equation

HRID 854536 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>>[CH3:12][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

3

Reactant 2

HCID 887MethanolHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 39129Methyl 3-Hydroxyphenylacetate

Procedure

(3-Hydroxy-phenyl)-acetic acid (5.0 g, 32.86 mmol) is stirred in methanol (100 mL) and concentrated (98%) sulfuric acid (3.0 mL) is added. The mixture is heated to reflux 18 hr. The reaction is cooled and concentrated. The residue is diluted with water (100 mL) and extracted with ethyl acetate (3×50 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, and concentrated to yield the title compound as an orange oil, 5.46 g, 100%. MS M++1 167. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. concentrationconcentrated (98%) sulfuric acid (3.0 mL)
  2. additionis added
  3. temperatureThe mixture is heated
  4. temperatureto reflux 18 hr
  5. temperatureThe reaction is cooled
  6. concentrationconcentrated
  7. additionThe residue is diluted with water (100 mL)
  8. extractionextracted with ethyl acetate (3×50 mL)
  9. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-4d0ea606c3c44832a1edb30512634704
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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