Benzyl Bromide → 3-(Benzyloxy)benzoic acid

HRID 1169432Notes

Reaction equation

HRID 1169432 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7]CC)=[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+]>CC(C)=O>[CH2:13]([O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([OH:7])=[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 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 3092263-(Benzyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture comprising ethyl 3-hydroxybenzoate (5.00 g), benzyl bromide (4.29 ml), potassium carbonate (6.24 g) and acetone (50 ml) was stirred at room temperature for 16 hours. After the reaction mixture was evaporated under reduced pressure to remove the solvent, water (200 ml) was added to the residue, and the resulting mixture was extracted with ethyl acetate. After the organic layer was concentrated, a 1 N aqueous solution of sodium hydroxide (50 ml) was added to the residue dissolved in methanol (50 ml), and the resulting mixture was heated at reflux for 2 hours. After cooling to room temperature, the reaction mixture was acidified by the addition of concentrated hydrochloric acid and was then extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride, was dried with anhydrous sodium sulfate and was then evaporated under reduced pressure to remove the solvent. The resulting residue was recrystallized from ethyl acetate/hexane to obtain 3-benzyloxybenzoic acid (5.10 g) as colorless crystals.

Workup

  1. customAfter the reaction mixture was evaporated under reduced pressure
  2. customto remove the solvent, water (200 ml)
  3. additionwas added to the residue
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. concentrationAfter the organic layer was concentrated
  6. additiona 1 N aqueous solution of sodium hydroxide (50 ml) was added to the residue
  7. dissolutiondissolved in methanol (50 ml)
  8. temperaturethe resulting mixture was heated
  9. temperatureat reflux for 2 hours
  10. additionthe reaction mixture was acidified by the addition of concentrated hydrochloric acid
  11. extractionwas then extracted with ethyl acetate
  12. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  13. dry with materialwas dried with anhydrous sodium sulfate
  14. customwas then evaporated under reduced pressure
  15. customto remove the solvent
  16. customThe resulting residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d9832d50184c43dcafa3cf47751a3f9a
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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