Hydrochloric Acid → HCID 23679658, compound

HRID 1086348Notes

Reaction equation

HRID 1086348 reaction equation
[OH-].[Na+:2].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:15])[C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1.[CH3:16]I.Cl>CO>[O:15]=[C:11]([CH:10]([C:7]1[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=1)[CH3:16])[C:12]([O-:14])=[O:13].[Na+:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium Hydroxide2×HCID 573193HCID 573193, compound

Product 1

HCID 23679658HCID 23679658, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3N aqueous solution of sodium hydroxide (5.0 ml, 15 mmoles) and 20 ml of methanol were added to p-fluorophenylpyruvic acid (0.92 g, 5.0 mmoles) to form a solution. Then, 2.0 ml of methyl iodide was added, and the mixture was stirred at room temperature for 14 hours. The reaction 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 concentrated under reduced pressure to give a pale yellowish white solid. To the product was added 2 ml of a 3N aqueous solution of sodium hydroxide, and the mixture was concentrated under reduced pressure. Ether was added to the resulting semi-solid mixture, and the precipitated sodium 2-oxo-3-(p-fluorophenyl)butanoate was isolated by filtration as a white solid (yield 26 %).

Workup

  1. customto form a solution
  2. extractionextracted with three 30 ml portions of ether
  3. dry with materialThe ether layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a pale yellowish white solid
  6. concentrationthe mixture was concentrated under reduced pressure
  7. additionEther was added to the resulting semi-solid mixture

Sources & evidence

ORD record
ord-2d0f604e3ac94f6a84f672096185c851
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

Loading…