Benzyl Bromide → (3-Benzyloxyphenyl)acetic acid

HRID 2281247Notes

Reaction equation

HRID 2281247 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+]>C1COCC1>[CH2:12]([O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 121223'-Hydroxyphenylacetic acidHCID 14797Potassium Hydroxide

Product 1

HCID 4592030(3-Benzyloxyphenyl)acetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(3-hydroxyphenyl)acetic acid (0.6 g, 3.95 mmol), benzyl bromide (0.710 g, 4.14 mmol), potassium hydroxide (0.550 g, 9.87 mmol), KI (13 mg, 0.079 mmol) in THF (20 mL) was refluxed for 18 h. The solvent was removed and the residue was dissolved in 50 mL of water and extracted with ether. The aqueous layer was acidified with aqueous 1N HCl and the white precipitate that formed was filtered off to afford 2-(3-(benzyloxy)phenyl)acetic acid as a gray solid (0.87 g, 91%).

Workup

  1. temperaturewas refluxed for 18 h
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in 50 mL of water
  4. extractionextracted with ether
  5. customthe white precipitate that formed
  6. filtrationwas filtered off

Sources & evidence

ORD record
ord-a2278d7be78242908f4a6083f05808ef
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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