Iodoethane → Methyl 5-acetyl-2-ethoxybenzoate

HRID 327068Notes

Reaction equation

HRID 327068 reaction equation
I[CH2:2][CH3:3].[CH3:4][O:5][C:6](=[O:17])[C:7]1[CH:12]=[C:11]([C:13](=[O:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[OH:16].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:4][O:5][C:6](=[O:17])[C:7]1[CH:12]=[C:11]([C:13](=[O:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[O:16][CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 18536574Methyl 5-acetyl-2-ethoxybenzoateYield 89%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Iodoethane (16.4 g, 0.105 mol) was added to a stirred mixture of 5-acetyl-2-hydroxybenzoic acid methyl ester (10 g, 51.5 mol) and anhydrous potassium carbonate (14.4 g, 0.104 mol) in 2-butanone (200 ml) and the resulting mixture heated under reflux for 3 days. The solvent was removed by evaporation under vacuum and the residue partitioned between water (100 ml) and ethyl acetate (100 ml). The aqueous phase was removed and extracted with further ethyl acetate (4×100 ml). The organic solutions were combined, dried (Na2SO4) and evaporated under vacuum. The residue was chromatographed on silica gel (130 g), using a methanol in dichloromethane elution gradient (0-1% methanol), to give the title compound as colourless crystals (10.15 g, 89%) m.p. 50°-55° C. Found C,64.88; H,6.38. C12H14O4 requires C,64.85; H,6.35%.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 3 days
  3. customThe solvent was removed by evaporation under vacuum
  4. customthe residue partitioned between water (100 ml) and ethyl acetate (100 ml)
  5. customThe aqueous phase was removed
  6. extractionextracted with further ethyl acetate (4×100 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under vacuum
  9. customThe residue was chromatographed on silica gel (130 g)
  10. washa methanol in dichloromethane elution gradient (0-1% methanol)

Sources & evidence

ORD record
ord-56bf09700eed4f6ba5200807790a02e5
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

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