Methanol → Methyl 2-(4-hydroxy-3,5-dimethoxyphenyl)acetate

HRID 2382559Notes

Reaction equation

HRID 2382559 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[O:14][CH3:15].[CH3:16]O.S(=O)(=O)(O)O>C(OCC)(=O)C>[CH3:16][O:12][C:11](=[O:13])[CH2:10][C:5]1[CH:4]=[C:3]([O:14][CH3:15])[C:2]([OH:1])=[C:7]([O:8][CH3:9])[CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 780934-Hydroxy-3,5-dimethoxyphenylacetic acid

Product 1

HCID 57436869Methyl 2-(4-hydroxy-3,5-dimethoxyphenyl)acetateYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(4-Hydroxy-3,5-dimethoxy-phenyl)-acetic acid (9.5 g, 0.042 mmol) was added to methanol (260 mL) and sulfuric acid (8 mL). After completion of addition the reaction was heated at reflux overnight. The next day, the reaction mixture was cooled down and concentrated to yield a crude oil. The oil was re-dissolved in ethyl acetate, washed with water, brine, and dried over sodium sulfate, and filtered to be concentrated again. The crude material was purified using silica gel chromatography (50%:50% ethyl acetate:pentane) to yield the desired product (1.5 g, 75% yield based on recovered starting material).

Workup

  1. additionAfter completion of addition the reaction
  2. temperaturewas heated
  3. temperatureat reflux overnight
  4. temperatureThe next day, the reaction mixture was cooled down
  5. concentrationconcentrated
  6. customto yield a crude oil
  7. washwashed with water, brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationto be concentrated again
  11. customThe crude material was purified

Sources & evidence

ORD record
ord-d254ab28bb69467c9d6cf240da53ceb0
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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