Methyl iodide → 4-Benzyloxy-2-methoxybenzoic acid methyl ester
Reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:20]I.[H-].[Na+]>CN(C=O)C>[CH3:20][O:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 2-hydroxy-4-benzyloxybenzoate (50 g, 194 mmol) in dry DMF (500 mL) was added methyl iodide (30 mL, 2.5 eq) and the solution was cooled to 0° C. under argon. The solution was stirred at 0° C. and sodium hydride (60% dispersion in mineral oil, 12 g, 1.5 eq) was added in several portions over 15 minutes. The reaction was allowed to warm to ambient temperature with stirring over 18 hours. The reacton was quenched with 12 mL of acetic acid and the solvent was removed under reduced pressure. The residue was partitioned between methylene chloride (700 mL) and saturated sodium bicarbonate (700 mL) and the organic layer was washed with water (2×700 mL), brine, dried over MgSO4, and filtered. The solvent was removed under reduced pressure to give methyl 2-methoxy-4-benzyloxybenzoate as a crystalline solid in 90% yield.
Workup
- temperatureto warm to ambient temperature
- stirringwith stirring over 18 hours
- customThe reacton was quenched with 12 mL of acetic acid
- customthe solvent was removed under reduced pressure
- customThe residue was partitioned between methylene chloride (700 mL) and saturated sodium bicarbonate (700 mL)
- washthe organic layer was washed with water (2×700 mL), brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-beb6581d8b99425d8bbc2e3dd7e0ae1e
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665719
Reaction notes
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