Ethanol → Ethyl 2-(3,5-dimethoxyphenyl)acetate

HRID 1383365Notes

Reaction equation

HRID 1383365 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.OS(O)(=O)=O.[CH3:20][CH2:21]O>>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][C:12]([O:14][CH2:20][CH3:21])=[O:13])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 138316(3,5-Dimethoxyphenyl)acetic acid

Product 1

HCID 11831071Ethyl 2-(3,5-dimethoxyphenyl)acetateYield 88%

Procedure

A solution of 3,5-dimethoxyphenylacetic acid (2.0 g; 10 mmol) and H2SO4 (conc.; 0.2 mL) in EtOH (50 mL) was refluxed overnight. The solution was concentrated, and the resultant material was dissolved in aqueous NaOH (1M). After extraction with ether (2×75 mL), washing of the combined organic phase with brine, drying (Na2SO4) and evaporating, 2.0 g (88%) of the sub-title compound was obtained.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe resultant material was dissolved in aqueous NaOH (1M)
  3. extractionAfter extraction with ether (2×75 mL)
  4. washwashing of the combined organic phase with brine
  5. dry with materialdrying (Na2SO4)
  6. customevaporating

Sources & evidence

ORD record
ord-9d499a4c79b14243a2a77ae77e2229ed
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

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