Methyl iodide → Methyl 3-hydroxy-5-methoxybenzoate

HRID 1594970Notes

Reaction equation

HRID 1594970 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:13]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 13941268Methyl 3-hydroxy-5-methoxybenzoateYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of methyl 3,5-dihydroxybenzoate (2.0 g, 11.9 mmol), K2CO3 (1.6 g, 11.9 mmol), and iodomethane (1.7 g, 11.9 mmol) in acetone (100 mL) was stirred at reflux. After stirring for three hours the mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography to yield the title compound as a white solid (0.813 g, 4.4 mmol). 1H NMR (400 MHz, CDCl3) δ 7.16 (m, 1H), 7.12 (m, 1H), 6.61 (m, 1H), 5.04 (s, 1H), 3.91 (s, 3H), 3.82 (s, 3H).

Workup

  1. temperatureat reflux
  2. stirringAfter stirring for three hours the mixture
  3. customwas partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e09b2ea21f754cb792ea221cd53374b2
Source dataset
uspto-grants-2001_09
Patent number
US06284777B1

Reaction notes

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