Potassium Hydroxide → [3-(Furan-2-yl)phenyl]acetic acid

HRID 495352Notes

Reaction equation

HRID 495352 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=1.[OH-].[K+]>CC(C)=O.O.[OH-].[Na+]>[O:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:16])=[O:2])[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 22326467HCID 22326467, compound

Product 1

HCID 22326464[3-(Furan-2-yl)phenyl]acetic acidYield 100%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-(2-furyl)phenylacetic acid methyl ester (0.047 g, 0.217 mmol, 1.0 eq) in acetone (3.0 ml) was added potassium hydroxide (0.5 ml of a 30% solution in H2O). The mixture was stirred at room temperature for 16 hours before diluting with 1 N NaOH (10 ml), and washing with CH2Cl2 (15 ml). The aqueous phase was acidified with 1 N HCl (15 ml) and the organics extracted with CH2Cl2 (3×20 ml). The extract was dried (Na2SO4) and concentrated under reduced pressure to yield 3-(2-furyl)phenylacetic acid (0.043 g, 100%) as a white solid; 1H-NMR (CDCl3, 400 MHz): δ 7.60 (1H, br s), 7.46 (1H, t, J=1.0 Hz), 7.34 (1H, t, J=7.5 Hz), 7.19 (2H, m), 6.65 (1H, d, J=3.2 Hz), 6.46 (1H, m), 3.67 (2H, s).

Workup

  1. washwashing with CH2Cl2 (15 ml)
  2. extractionthe organics extracted with CH2Cl2 (3×20 ml)
  3. dry with materialThe extract was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01219f47adf749198b83d1994ec8c246
Source dataset
uspto-grants-2005_09
Patent number
US06939861B2

Reaction notes

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