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

HRID 1671

Reaction equation

HRID 1671 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 (12 g, 46 mmol) in DMF (150 mL) was added NaH (2.76 g, 69 mmol) and methyl iodide (7.2 mL, 116 mmol). The solution was allowed to warm to ambient temperature overnight with stirring. The reaction mixture was poured onto ice and the resulting aqueous solution extracted with Et2O (3×200 mL). The organic phase was dried (MgSO4), filtered and the Et2O removed under reduced pressure. The crude white solid was purified by pressurized silica gel column chromatography using 4:1 hexanes:EtOAc. Evaporation of the hexanes:EtOAc mixture gave the desired methyl 4-benzyloxy-2-methoxybenzoate as a white powder.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionthe resulting aqueous solution extracted with Et2O (3×200 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe Et2O removed under reduced pressure
  6. customThe crude white solid was purified by pressurized silica gel column chromatography
  7. customEvaporation of the hexanes

Sources & evidence

ORD record
ord-c4670bc17b3d4dddbc6d0f72787fbc62
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Linked notes

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