Water → 5-(2,3,4-Trimethoxyphenyl)-5-oxovaleric acid

HRID 33954Notes

Reaction equation

HRID 33954 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:23])[CH2:6][CH2:7][CH2:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[C:11]=1[O:20][CH3:21].O>CO>[O:22]=[C:9]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[C:11]=1[O:20][CH3:21])[CH2:8][CH2:7][CH2:6][C:5]([OH:23])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 689200075-Oxo-5-(2,3,4-trimethoxy-phenyl)-pentanoic acid methyl ester

Product 1

HCID 193481585-(2,3,4-Trimethoxyphenyl)-5-oxovaleric acidYield 109.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.78 g of sodium hydroxide was dissolved in 25 mL of methanol in a 100 mL round bottom flask. The reaction mixture was cooled to room temperature and 60 (6.78 g, 22.90 mmol) was added followed by 5 mL of water 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 EA:Hex) to yield 7.05 g of 61 (quantitative yield).

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 EA:Hex)

Sources & evidence

ORD record
ord-87723e92f7c64e559a691aa795a7e25d
Source dataset
uspto-grants-2008_09
Patent number
US07429681B2

Reaction notes

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