Hydrochloric Acid → HCID 15023988, compound

HRID 1086352Notes

Reaction equation

HRID 1086352 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=[O:16])[C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1.[CH3:17]I.Cl>CO>[O:16]=[C:12]([CH:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][CH:9]=1)[CH3:17])[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 5784733-(4-Methoxyphenyl)-2-oxopropanoic acid

Product 1

HCID 15023988HCID 15023988, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1N aqueous solution of sodium hydroxide (20 ml; 20 mmoles) was slowly added to 1.94 g (10 mmoles) of p-methoxyphenylpyruvic acid and a solution of 1.0 ml of methyl iodide in 50 m 1 of methanol. After addition, the mixture was stirred at room temperature for 4 hours. The mixture was acidified with 1N hydrochloric acid and extracted with three 30 ml portions of ether. The ether layers were dried over magnesium sulfate, and the ether was evaporated under reduced pressure to give a pale yellowish white solid. The NMR spectral analysis of this product led to the determination that this product was nearly pure 2-oxo-3-(p-methoxyphenyl)butanoic acid (1.40 g; yield 67 %).

Workup

  1. additionAfter addition
  2. extractionextracted with three 30 ml portions of ether
  3. dry with materialThe ether layers were dried over magnesium sulfate
  4. customthe ether was evaporated under reduced pressure
  5. customto give a pale yellowish white solid

Sources & evidence

ORD record
ord-836962916fe64154955bab244a38eb67
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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