Benzyl Bromide → Methyl 3-(benzyloxy)-5-hydroxybenzoate

HRID 507947Notes

Reaction equation

HRID 507947 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:13]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoateYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3,5-dihydroxybenzoate (8.41 g, 50.0 mmol) and benzyl bromide (3.57 mL, 30.0 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.15 g, 30.0 mmol), and the mixture was stirred under a nitrogen atmosphere at 70° C. for 16 hr. The reaction mixture was concentrated under reduced pressure, and water was added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-30% ethyl acetate/hexane) and recrystallized from ethyl acetate-hexane to give the title compound (3.56 g, yield 46%) as colorless prism crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (5%-30% ethyl acetate/hexane)
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-cd6369a01de349feaa40f3ec4b0092ec
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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