Potassium Carbonate → HCID 18536595, compound

HRID 412045Notes

Reaction equation

HRID 412045 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][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:16][CH2:17][CH3:18])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-Iodopropane2×HCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 18536595HCID 18536595, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred mixture of methyl 5-acetyl-2-hydroxy-benzoate (10 g, 0.0515 mol), 1-iodopropane (10.5 g, 0.0618 mol), anhydrous potassium carbonate (14.2 g, 0.103 mol) and 2-butanone (200 ml) was heated under reflux for 18 hours. A further quantity of 1-iodopropane (10.5 g, 0.0618 mol) was then added and heating under reflux continued for a further 24 hours. The solvent was removed by evaporation under vacuum and the residue partitioned between water (200 ml) and ethyl acetate (200 ml). The aqueous phase was extracted with ethyl acetate (2×100 ml), then the organic solutions combined, dried (Na2SO4) and evaporated under vacuum. The residue was chromatographed on silica gel (120 g) using a methanol in dichloromethane elution gradient (0-1%), then crystallization of the product from ethyl acetate-hexane gave the title compound as white crystals (6.85 g, 56%), m.p. 49° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. customThe solvent was removed by evaporation under vacuum
  6. customthe residue partitioned between water (200 ml) and ethyl acetate (200 ml)
  7. extractionThe aqueous phase was extracted with ethyl acetate (2×100 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated under vacuum
  10. customThe residue was chromatographed on silica gel (120 g)
  11. washa methanol in dichloromethane elution gradient (0-1%)
  12. customcrystallization of the product from ethyl acetate-hexane

Sources & evidence

ORD record
ord-be8f6987dad94d5daecfa80b1d637f16
Source dataset
uspto-grants-2003_05
Patent number
US06562830B1

Reaction notes

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