Ethanol → Ethyl (2,3-dimethoxyphenyl)acetate

HRID 1760035Notes

Reaction equation

HRID 1760035 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([OH:14])=[O:13].OS(O)(=O)=O.[CH3:20][CH2:21]O>>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([O:14][CH2:20][CH3:21])=[O:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1359642,3-Dimethoxyphenylacetic acid

Product 1

HCID 254443Ethyl (2,3-dimethoxyphenyl)acetate

Procedure

To a solution of 2,3-dimethoxyphenylacetic acid (2.52 g, 12.8 mmol) in EtOH (abs.; 20 mL) was added H2SO4 (30 μL), and the solution was refluxed for 20 hours. The resultant solution was concentrated, dissolved in ether, and the ether solution was washed with NaHCO3/aq (2×30 mL) and brine, dried (MgSO4) and concentrated to yield the sub-title compound.

Workup

  1. temperaturethe solution was refluxed for 20 hours
  2. concentrationThe resultant solution was concentrated
  3. dissolutiondissolved in ether
  4. washthe ether solution was washed with NaHCO3/aq (2×30 mL) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-867a980267414fd5bf7a91700d3b0b58
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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