Iodoethane → Methyl 5-acetyl-2-ethoxybenzoate

HRID 412040Notes

Reaction equation

HRID 412040 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].I[CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:16][CH3:17])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 18536574Methyl 5-acetyl-2-ethoxybenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred mixture of methyl 5-acetyl-2-hydroxy-benzoate (10 g, 0.052 mol), iodoethane (16.4 g, 0.104 mol), anhydrous potassium carbonate (14.4 g, 0.104 mol) and 2-butanone (200 ml) was heated under reflux for 3 days. The solvent was then removed by evaporation under vacuum, the residue dissolved in water (200 ml) and this solution extracted with ethyl acetate (4×200 ml). The organic fractions were combined, washed with brine (2×200 ml), dried (Na2SO4) and evaporated under vacuum, then the residue chromatographed on silica gel (130 g) using a methanol in dichloromethane elution gradient (0-1%). Crystallization of the product from ethyl acetate-hexane gave the title compound as colourless crystals (10.15 g, 88%), m.p. 50-55° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 days
  3. customThe solvent was then removed by evaporation under vacuum
  4. dissolutionthe residue dissolved in water (200 ml)
  5. extractionthis solution extracted with ethyl acetate (4×200 ml)
  6. washwashed with brine (2×200 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under vacuum
  9. customthe residue chromatographed on silica gel (130 g)
  10. washa methanol in dichloromethane elution gradient (0-1%)
  11. customCrystallization of the product from ethyl acetate-hexane

Sources & evidence

ORD record
ord-46c7f248094748af84930e9a995aad8d
Source dataset
uspto-grants-2003_05
Patent number
US06562830B1

Reaction notes

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