Iodoethane → 3,4-Dimethoxy-5-ethoxybenzoic Acid

HRID 323462Notes

Reaction equation

HRID 323462 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([OH:14])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH2:21](I)[CH3:22].[OH-].[K+]>CC(C)=O.C(O)C.O.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH2:21][CH3:22])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7]

Participants

9

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 747093-Hydroxy-4,5-Dimethoxybenzoic Acid

Product 1

HCID 184645383,4-Dimethoxy-5-ethoxybenzoic Acid

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Combine 3,4-dimethoxy-5-hydroxybenzoic acid (1.0 g, 5.0 mmol), potassium carbonate (4.2 g, 30.2 mmol), and ethyl iodide (3.9 g, 25.2 mmol) in acetone (50 mL). Heat to reflux. After 24 hours, cool, add methanol (25 mL) and water (5 mL) After 18 hours, concentrate in vacuo to give a residue. Combine the residue and ethanol (50 mL) and potassium hydroxide (0.56 g, 10 mmol). After 18 hours, concentrate in vacuo to give a residue. Partition the residue between ethyl acetate and a 1 M aqueous solution of hydrochloric acid. Extract the aqueous layer three times with ethyl acetate. Combine the organic layers, dry over Na2SO4, filter, and concentrate in vacuo to give a residue. Triturate the residue to give a solid. Collect the solid to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. concentrationconcentrate in vacuo
  4. customto give a residue
  5. waitAfter 18 hours
  6. concentrationconcentrate in vacuo
  7. customto give a residue
  8. customPartition the residue between ethyl acetate
  9. extractionExtract the aqueous layer three times with ethyl acetate
  10. dry with materialdry over Na2SO4
  11. filtrationfilter
  12. concentrationconcentrate in vacuo
  13. customto give a residue
  14. customTriturate the residue
  15. customto give a solid
  16. customCollect the solid

Sources & evidence

ORD record
ord-3036a5326d3f4426b39da47486114bac
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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