2-Bromopropane → (3-Benzyloxyphenyl)acetic acid

HRID 2274909Notes

Reaction equation

HRID 2274909 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.Br[CH:13]([CH3:15])[CH3:14].[OH-].[K+]>CCO>[CH2:14]([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:15]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 121223'-Hydroxyphenylacetic acidHCID 14797Potassium Hydroxide

Product 1

HCID 4592030(3-Benzyloxyphenyl)acetic acidYield 70.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 2-(3-hydroxyphenyl)acetic acid (0.800 g, 5.26 mmol), 2-bromopropane (0.971 g, 7.89 mmol), potassium hydroxide (0.740 g, 13.2 mmol), KI (18 mg, 0.11 mmol) in 20 mL EtOH 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 extracted with EtOAc. The organic layers were dried (Na2SO4) and concentrated to afford a residue which was purified by silica gel chromatography (petroleum ether/EtOAc 4:1) to get 2-(3-(benzyloxy)phenyl)acetic acid as a white solid (0.45 g, 44%).

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. extractionextracted with EtOAc
  6. dry with materialThe organic layers were dried (Na2SO4)
  7. concentrationconcentrated
  8. customto afford a residue which
  9. customwas purified by silica gel chromatography (petroleum ether/EtOAc 4:1)

Sources & evidence

ORD record
ord-4ba722232c1640edb3fbe4e7a24714c3
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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