Hydrochloric Acid → HCID 15023993, compound

HRID 1086353Notes

Reaction equation

HRID 1086353 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=[O:19])[C:15]([O:17]C)=[O:16])=[CH:9][CH:8]=1)=[O:6].[CH3:20]I.Cl>O1CCCC1>[O:19]=[C:14]([CH:13]([C:10]1[CH:11]=[CH:12][C:7]([C:5]([OH:4])=[O:6])=[CH:8][CH:9]=1)[CH3:20])[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 15023992HCID 15023992, compound

Product 1

HCID 15023993HCID 15023993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3N aqueous solution of sodium hydroxide (20 ml; 60 mmoles) was added to 4.82 g (20 mmoles) of methyl p-methoxycarbonylphenylpyruvate, and the mixture was stirred at room temperature for 30 minutes. Then, 50 ml of tetrahydrofuran and 3.0 ml of methyl iodide were added, and the mixture was reacted at room temperature for 12 hours. After the reaction, the reaction mixture was acidified with 1N of hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a yellowish white solid of 2-oxo-3-(p-hydroxycarbonylphenyl)butanoic acid. 3N sodium hydroxide (5.5 ml) was added to the resulting solid, and the mixture was concentrated under reduced pressure, and then ether was added. Sodium 2-oxo-3-(p-hydroxycarbonylphenyl)butanoate (4.18 g; yield 88 %) which precipitated was isolated by filtration.

Workup

  1. customthe mixture was reacted at room temperature for 12 hours
  2. customAfter the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3af5440ecf694cc08f05e27b43ef9547
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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