Benzyl Bromide → Methyl 4-(benzyloxy)-3-methoxybenzoate

HRID 19990

Reaction equation

HRID 19990 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:17][CH3:18])[CH:11]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O>[CH3:7][O:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:12]([O:17][CH3:18])[CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19844Methyl Vanillate

Product 1

HCID 5059267Methyl 4-(benzyloxy)-3-methoxybenzoateYield 86.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (3.45 g; 25 mmol) was added to a solution of 4-hydroxy-3-methoxy benzoic acid methyl ester (3.6 g; 20 mmol) and benzyl bromide (3.42 g; 20 mmol) in acetone (100 ml). The reaction mixture was refluxed for 12 hrs. After the removal of the solvent under reduced pressure, the residue was partitioned between ethyl acetate (150 ml) and water (50 ml). The ethyl acetate layer was washed with water (50 ml) and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure provided 4.64 g of 4-benzyloxy-3-methoxy benzoic acid methyl ester (Yield=86.6%)

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hrs
  2. customAfter the removal of the solvent under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (150 ml) and water (50 ml)
  4. washThe ethyl acetate layer was washed with water (50 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-7d3a11347ef24425bdf9b987028eb8a0
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Linked notes

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