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

HRID 2109388Notes

Reaction equation

HRID 2109388 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH3:27]>CC(C)=O>[CH2:1]([O:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19844Methyl Vanillate

Product 1

HCID 5059267Methyl 4-(benzyloxy)-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (3.59 ml) and potassium carbonate (5.69 g) were added to an acetone (50 ml) solution of methyl 4-hydroxy-3-methoxybenzoate (5.00 g), and heated at reflux for 4 hours. After removing solid matter by filtration and concentrating the filtrate under reduced pressure, the residue was dissolved in ethyl acetate, and washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure, thereby giving 7.47 g of methyl 4-benzyloxy-3-methoxybenzoate.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. customAfter removing solid matter
  4. filtrationby filtration
  5. concentrationconcentrating the filtrate under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  8. dry with materialThe organic layer was dried over MgSO4
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ee087a14b711406eb1969650aa83c6bf
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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