Methyl iodide → Methyl 4-iodo-3-methoxybenzoate

HRID 2416587Notes

Reaction equation

HRID 2416587 reaction equation
[OH:1][C:2]1[CH:3]=C([CH:8]=[CH:9][C:10]=1[I:11])C(O)=O.CI.[C:14](=O)([O-])[O-].[K+].[K+].[C:20]([O:23][CH2:24]C)(=[O:22])[CH3:21]>CN(C=O)C>[I:11][C:10]1[CH:9]=[CH:8][C:21]([C:20]([O:23][CH3:24])=[O:22])=[CH:3][C:2]=1[O:1][CH3:14]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 7368543-Hydroxy-4-iodobenzoic acid

Product 1

HCID 11243290Methyl 4-iodo-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

14.9 g (56.4 mmol) of 3-hydroxy-4-iodobenzoic acid was dissolved in 200 ml of DMF. 17.5 ml (282 mmol) of methyl iodide and 39 g (282 mmol) of potassium carbonate was added to the obtained solution, and they were stirred at 50° C. for 3 hours. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-8f6497f51d4647b592b69c9411521880
Source dataset
uspto-grants-2004_11
Patent number
US06825181B1

Reaction notes

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