Water → Methyl 4-Formylbenzoate

HRID 2269807Notes

Reaction equation

HRID 2269807 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[C:7]([OH:17])(=[O:16])[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.CI.O>CN(C)C=O>[CH:12]([C:11]1[CH:14]=[CH:15][C:8]([C:7]([O:17][CH3:1])=[O:16])=[CH:9][CH:10]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 120884-Formylbenzoic acid

Product 1

HCID 15294Methyl 4-FormylbenzoateYield 84.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Anhydrous potassium carbonate (4.7 g) is added to a solution of terephthalaldehydic acid (5.1 g) in anhydrous dimethylformamide (110 ml), and the mixture is stirred at room temperature for 10 minutes. Then, methyl iodide (2.5 ml) is added thereto, and the mixture is stirred overnight. Water is added to the reaction mixture, and the whole is extracted with ethyl acetate. The organic layer is washed with water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give 4.7 g (84%) of methyl 4-formylbenzoate as crystals.

Workup

  1. stirringthe mixture is stirred overnight
  2. extractionthe whole is extracted with ethyl acetate
  3. washThe organic layer is washed with water and saturated brine successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e1e323cc1e974870afef90f1183cc00e
Source dataset
uspto-grants-2001_12
Patent number
US06329547B1

Reaction notes

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