Dimethylformamide → Methyl 3-formyl-4-methoxybenzoate

HRID 1684618Notes

Reaction equation

HRID 1684618 reaction equation
[CH3:1]I.[CH:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[OH:14])C(O)=O)=[O:4].[C:15]([O-:18])([O-])=O.[K+].[K+].CN(C)[CH:23]=[O:24]>O>[CH3:15][O:18][C:23](=[O:24])[C:7]1[CH:11]=[CH:12][C:13]([O:14][CH3:1])=[C:5]([CH:3]=[O:4])[CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2717613-Formyl-4-hydroxybenzoic acid

Product 1

HCID 15192109Methyl 3-formyl-4-methoxybenzoateYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

24.8 mL (398 mmol) of methyl iodide were added dropwise to a room temperature suspension of 30.0 g (181 mmol) of 3-formyl-4-hydroxybenzoic acid (from Example 36) and 75 g (542 mmol) of K2CO3 in 250 mL of dry dimethylformamide (DMF). After stirring 4 hours at room temperature, the reaction mixture was diluted with 2 L H2O and extracted four times with 750 mL ethyl acetate. The ethyl acetate extracts were washed three times with 500 mL H2O, one time with 300 mL 1N NaOH, one time with 500 mL H2O, one time with 250 mL brine, and dried over Na2SO4. Filtration, concentration of filtrate and drying under vacuum gave 20.35 g of pure product as pale yellow needles. 58% yield.

Workup

  1. extractionextracted four times with 750 mL ethyl acetate
  2. washThe ethyl acetate extracts were washed three times with 500 mL H2O, one time with 300 mL 1N NaOH, one time with 500 mL H2O, one time with 250 mL brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration, concentration of filtrate
  5. customdrying under vacuum

Sources & evidence

ORD record
ord-059413e90e48456eaefe86d65d18037f
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

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