Water → 4-(3-Methoxy-4-methylphenyl)butanoic acid

HRID 1859810Notes

Reaction equation

HRID 1859810 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][CH2:12][C:13]#N)[CH:6]=[CH:7][C:8]=1[CH3:9].[OH-:15].[Na+].[OH2:17]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][CH2:12][C:13]([OH:17])=[O:15])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 186265273-(3-Methoxy-4-methylphenyl)propyl cyanide

Product 1

HCID 186264724-(3-Methoxy-4-methylphenyl)butanoic acidYield 75.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.75 g (35.7 mmol) of 3-(3-methoxy-4-methylphenyl)propyl cyanide in 75 mL of EtOH was treated with a solution of 8.0 g (0.2 mol) of NaOH in 40 mL of H2O and heated at reflux overnight. The solvent was removed under reduced pressure and the residue taken up in H2O. After washing with Et2O, the aqueous solution was acidified to the Congo Red end point with dilute HCl. A white solid separated which was collected and dried. There was obtained 5.6 g (75.5% yield) of the product, mp 69-70° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 209 (M+H+).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. washAfter washing with Et2O
  5. customA white solid separated which
  6. customwas collected
  7. customdried

Sources & evidence

ORD record
ord-d35388fc753b470e8c82307ff2110a18
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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