Methyl iodide → Methyl 3-hydroxy-5-methoxy-4-methylbenzoate

HRID 1831829Notes

Reaction equation

HRID 1831829 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([CH3:11])=[C:6]([OH:12])[CH:5]=1.[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:5]=[C:6]([O:12][CH3:14])[C:7]([CH3:11])=[C:8]([OH:10])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11458051Methyl 3,5-dihydroxy-4-methylbenzoate

Product 1

HCID 11389966Methyl 3-hydroxy-5-methoxy-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.1 g (28.2 mmol) of 3,5-Dihydroxy-4-methyl-benzoic acid methyl ester was dissolved in 100 ml of DMF and treated at 0° C. with 7.8 g (56.4 mmol) of potassium carbonate and 4.0 g (28.2 mmol) of methyl iodide. The solution was stirred for 16 h at RT. The solvent was removed under reduced pressure, the residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The compound was purified by preparative RP-HPLC eluting with a gradient of 0 to 100% acetonitrile in water (+0.01% trifluoroacetic acid).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe solution was washed three times with water
  3. dry with materialThe organic phase was dried with magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe compound was purified by preparative RP-HPLC
  7. washeluting with a gradient of 0 to 100% acetonitrile in water (+0.01% trifluoroacetic acid)

Sources & evidence

ORD record
ord-988e831645e74be095422ad7772c83d1
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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