Potassium Iodide → Methyl 4-methoxy-2-propoxybenzoate

HRID 1460974Notes

Reaction equation

HRID 1460974 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8].Br[CH2:15][CH2:16][CH3:17].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([O:13][CH2:15][CH2:16][CH3:17])[CH:4]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 79523Methyl 4-methoxysalicylate

Product 1

HCID 21250797Methyl 4-methoxy-2-propoxybenzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of methyl 4-methoxysalicylate (25 g), bromopropane (15.6 ml), potassium iodide (2.82 g) and anhydrous potassium carbonate (27.53 g) was heated under reflux for 48 hours. The cooled reaction mixture was filtered and the filtrate was evaporated under reduced pressure to yield an oil which was dissolved in diethyl ether (200 ml). The ethereal solution was extracted with aqueous sodium hydroxide to remove unreacted starting material and the organic phase was then washed with water and brine, dried (magnesium sulphate) and evaporated under reduced pressure to yield methyl 4-methoxy-2-propoxybenzoate, 22.45 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customthe filtrate was evaporated under reduced pressure
  6. customto yield an oil which
  7. extractionThe ethereal solution was extracted with aqueous sodium hydroxide
  8. customto remove unreacted
  9. washthe organic phase was then washed with water and brine
  10. dry with materialdried (magnesium sulphate)
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bb21f7a10ca3490a95cfe0880b422987
Source dataset
uspto-grants-1991_12
Patent number
US05073559

Reaction notes

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