3'-Hydroxyphenylacetic acid → 1247920-77-9

HRID 2281249Notes

Reaction equation

HRID 2281249 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[CH2:13][CH:14]1[CH2:16][CH2:15]1.[OH-].[K+]>CCO>[CH:14]1([CH2:13][O:1][C:2]2[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 121223'-Hydroxyphenylacetic acidHCID 14797Potassium HydroxideHCID 81503Bromomethylcyclopropane

Product 1

HCID 613980661247920-77-9Yield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 2-(3-hydroxyphenyl)acetic acid (1.0 g, 6.6 mmol), (bromomethyl)cyclopropane (0.97 g, 7.2 mmol), potassium hydroxide (0.920 g, 16.4 mmol), KI (22 mg, 0.13 mmol) in EtOH (20 mL) was refluxed for 18 h. The solvent was removed in vacuo, 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-(cyclopropylmethoxy)phenyl)acetic acid as a white solid (0.80 g, 59%).

Workup

  1. temperaturewas refluxed for 18 h
  2. customThe solvent was removed in vacuo
  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-79f90a0444794671b9d6ab3645baa97b
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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