Water → 4-(2,3,4-TRIMETHOXYPHENYL)-4-OXOBUTYRIC ACID

HRID 1944646Notes

Reaction equation

HRID 1944646 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:22])[CH2:6][CH2:7][C:8](=[O:21])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[C:10]=1[O:19][CH3:20].O>CO>[O:21]=[C:8]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[C:10]=1[O:19][CH3:20])[CH2:7][CH2:6][C:5]([OH:22])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 447204584-Oxo-4-(2,3,4-trimethoxy-phenyl)-butyric acid methyl ester

Product 1

HCID 109454324-(2,3,4-TRIMETHOXYPHENYL)-4-OXOBUTYRIC ACIDYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5.95 g of sodium hydroxide was dissolved in 200 mL of methanol in a 500 mL round bottom flask. The reaction mixture was cooled to room temperature and 55 (6.78 g, 22.90 mmol) was added followed by 20 mL of water and 100 mL of methanol and the reaction mixture was refluxed for 30 min. The solvent was evaporated under reduced pressure and the reaction mixture was neutralized with dilute hydrochloric acid and the reaction mixture was extracted with ether (100×3) and the combined organic phases were washed with water and dried over sodium sulfate and solvent evaporated under reduced pressure. The crude product was purified by column chromatography (20:80 EtOAc:Hexanes) to yield 5.43 g of 56 as tan colored solid (94%).

Workup

  1. temperaturethe reaction mixture was refluxed for 30 min
  2. customThe solvent was evaporated under reduced pressure
  3. extractionthe reaction mixture was extracted with ether (100×3)
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over sodium sulfate and solvent
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography (20:80 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-f997928ab26c456ca625a9618626dec3
Source dataset
uspto-grants-2013_03
Patent number
US08394859B2

Reaction notes

Loading…