Water → 4-(2',3'-Dimethoxyphenyl) 3-phenylbutyric acid

HRID 233381

Reaction equation

HRID 233381 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][C:14]#N.[OH-:22].[Na+].[OH2:24]>C(O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][C:14]([OH:24])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 199611014-(2',3'-Dimethoxyphenyl)-3-phenylbutanenitrile

Product 1

HCID 124785434-(2',3'-Dimethoxyphenyl) 3-phenylbutyric acidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2',3'-Dimethoxyphenyl)-3-phenylbutanenitrile (20 g, 71 mmol), from Step 4, was dissolved in 1.5 L of ethanol. Sodium hydroxide (20 g, 0.5 mol) and 200 mL of water were added and the reaction mixture was heated at reflux temperature for 24 h. The solvent was removed in vacuo and 1 L of water plus 1 L of methylene chloride were added to the residue. The layers were separated and the organic layer discarded. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with 3 L of ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 21 g (98% yield) of the title compound as an oil; 1H NMR (CDCl3) δ: 2.6-2.7 (m, 2H), 2.9 (d, 2H), 3.4-3.5 (m, 1H), 3.72 (s, 3H), 3.82 (s, 3H), 6.6 (dd, 1H), 6.73 (dd, 1H), 6.88 (t, 1H), 7.1-7.3 (m, 5H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 24 h
  3. customThe solvent was removed in vacuo and 1 L of water plus 1 L of methylene chloride
  4. additionwere added to the residue
  5. customThe layers were separated
  6. extractionextracted with 3 L of ethyl acetate
  7. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de20507ff9aa4d49828923c54aec8c2b
Source dataset
uspto-grants-1997_01
Patent number
US05591884

Linked notes

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