Benzyl Bromide → Methyl 3,4-bis(benzyloxy)benzoate

HRID 19985

Reaction equation

HRID 19985 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([OH:17])[CH:11]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH3:7][O:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([O:17][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 287064Methyl 3,4-Dihydroxybenzoate

Product 1

HCID 10545660Methyl 3,4-bis(benzyloxy)benzoateYield 122.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (6.5 g; 47 mmol) was added to a solution of 3,4-dihydroxybenzoic acid methyl ester (2.6 g; 15.7 mmol) and benzyl bromide (5.37 g; 31.4 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 3.36 g of 3,4-Dibenzyloxy 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-076a4c27aa214e05aa3d5ab817536595
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Linked notes

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