Dimethyl Sulfoxide → Methyl 4-formyl-3-methoxybenzoate

HRID 924638Notes

Reaction equation

HRID 924638 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].[C:13]([O-:16])(O)=O.[Na+].[CH3:18]S(C)=O>C(Cl)Cl>[CH3:18][O:8][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([CH:13]=[O:16])=[C:3]([O:11][CH3:12])[CH:4]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 162158674-Bromo-3-methoxybenzoic acid

Product 1

HCID 10631650Methyl 4-formyl-3-methoxybenzoateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-bromo-3-methoxy-benzoic acid (15.0 g, 58 mmol) in DMSO (150 mL) was added NaHCO3 (20.0 g, 230 mmol). This was heated to 80° C. for 18 hours. The reaction was then cooled to room temperature and the solvent removed under reduced pressure. The crude reaction mixture was then dissolved in DCM (200 mL) and washed with 1N HCl (100 mL), water (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was sufficiently pure to use without further purification. The product, 4-formyl-3-methoxybenzoic acid methyl ester, was obtained in 79% yield (8.9 g, 45.8 mmol).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customthe solvent removed under reduced pressure
  3. customThe crude reaction mixture
  4. washwashed with 1N HCl (100 mL), water (100 mL), NaCl (sat.) (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customto use without further purification

Sources & evidence

ORD record
ord-2fbafbdf6f554d8bb54483a8547448e2
Source dataset
uspto-grants-2016_03
Patent number
US09283183B2

Reaction notes

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