Methyl iodide → Methyl 5-(benzyloxy)-2-methoxybenzoate

HRID 1644581Notes

Reaction equation

HRID 1644581 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:19])=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](=O)([O-])[O-].[Cs+].[Cs+].CI>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:19][CH3:20])=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 13026913Methyl 5-(benzyloxy)-2-hydroxybenzoate

Product 1

HCID 66775910Methyl 5-(benzyloxy)-2-methoxybenzoateYield 90.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspended solution of methyl 5-benzyloxy-2-hydroxybenzoate (3.91 g) and cesium carbonate (6.41 g) in acetone (100 ml) was added methyl iodide (1.41 ml), and the mixture was stirred at 50° C. for 6 hr. The reaction mixture was concentrated, dissolved again in ethyl acetate and washed with saturated brine. The organic layer was dried (over MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Biotage cartridge 40+M, ethyl acetate:n-hexane=15:85→1:4) to give methyl 5-benzyloxy-2-methoxybenzoate (3.72 g, 90%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved again in ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialThe organic layer was dried (over MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (Biotage cartridge 40+M, ethyl acetate:n-hexane=15:85→1:4)

Sources & evidence

ORD record
ord-c56eb20b3936404982766655e9276378
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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