Methyl iodide → 4-Benzyloxy-2-methoxybenzoic acid methyl ester

HRID 1292037Notes

Reaction equation

HRID 1292037 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([OH:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:22]I>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:19][CH3:22])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoate

Product 1

HCID 108260394-Benzyloxy-2-methoxybenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, 0° C. solution of methyl 4-benzyloxy-2-hydroxybenzoate (12g, 46 mmol) from step 1 above in DMF (150 mL) was added NaH (2.76 g of a 60% suspension in mineral oil, 69 mmol) and methyl iodide (7.2 mL, 116 mmol). The solution was warmed to ambient temperature and stirred for 18 h. The reaction mixture was poured onto ice and the resulting solution was extracted with ether (3×200 mL). The organic phase was dried (MgSO4), filtered and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 4:1 hexanes:EtOAc as eluant. Methyl 4-benzyloxy-2-methoxybenzoate was obtained as a white powder.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionthe resulting solution was extracted with ether (3×200 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-3ade541381ab4cf7b00337fa2ecc21fe
Source dataset
uspto-grants-1998_05
Patent number
US05756497

Reaction notes

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