Water → 4-(2,3,4-Trimethoxyphenyl)butanoic acid

HRID 1944648Notes

Reaction equation

HRID 1944648 reaction equation
[OH-:1].[Na+].O=[C:4]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[C:13]=1[O:22][CH3:23])[CH2:5][CH2:6][CH2:7]CC(O)=O.[OH2:24]>CO>[CH3:23][O:22][C:13]1[C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:12]=1[CH2:4][CH2:5][CH2:6][C:7]([OH:24])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 247271636-(2,3,4-Trimethoxyphenyl)-6-oxohexanoic acid

Product 1

HCID 435890914-(2,3,4-Trimethoxyphenyl)butanoic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

17 g of sodium hydroxide was dissolved in 200 mL of methanol in a 1000 mL round bottom flask. The reaction mixture was cooled to room temperature and 66 (6.78 g, 22.90 mmol) was added followed by 60 mL of water and 300 mL of anhydrous 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 (200×3) 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 (30:70 EA:Hex) to yield 12.86 g of 57 as pale yellow colored oil (78%). Rf: 0.15 (40:60 EtOAc:Hexanes).

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 (200×3)
  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 (30:70 EA:Hex)

Sources & evidence

ORD record
ord-050754c30f3140ea930720775c67378f
Source dataset
uspto-grants-2013_03
Patent number
US08394859B2

Reaction notes

Loading…