Methyl iodide → Methyl 5-formyl-2-methoxybenzoate

HRID 637137Notes

Reaction equation

HRID 637137 reaction equation
[CH:1]([C:3]1[CH:11]=C(C(O)=O)[C:6]([OH:12])=[CH:5][CH:4]=1)=[O:2].[C:13](=O)([O-])[O-].[K+].[K+].CI.[C:21]([O:24][CH2:25]C)(=[O:23])[CH3:22].CCCCCC>CC(C)=O>[CH3:13][O:12][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:11][C:22]=1[C:21]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 692265-Formylsalicylic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 10856352Methyl 5-formyl-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Combine 5-formylsalicylic acid (5.0 g, 30.1 mmol), potassium carbonate (16.6 g, 120.4 mmol), and methyl iodide (34.06 g, 240 mmol) in acetone (20 mL). Heat to reflux. After 12 hours, cool and extract five times with ethyl acetate. Combine the organic layers and extract with brine. Dry over MgSO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate/hexane 1/1 to give methyl 2-methoxy-5-formylbenzoate: Rf=0.44 (silica gel, 1/1 ethyl acetate/hexane).

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. extractionextract five times with ethyl acetate
  4. extractionextract with brine
  5. dry with materialDry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto give a residue

Sources & evidence

ORD record
ord-7f18e16cec9d4cfd8a134ebeaa12dd95
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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