Hydrochloric Acid → HCID 15024015, compound

HRID 1086367Notes

Reaction equation

HRID 1086367 reaction equation
[OH-].[Na+].[O:3]=[C:4]([CH:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[CH3:9])[C:5]([O-:7])=[O:6].[Na+].[CH2:18](Br)[C:19]#C.Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O1CCCC1>[O:3]=[C:4]([CH:8]([C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[CH2:9][C:18]#[CH:19])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 23676255HCID 23676255, compound

Product 1

HCID 15024015HCID 15024015, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 3N aqueous solution (0.9 ml) of sodium hydroxide and 5.0 ml of tetrahydrofuran were added to 0.50 g (2.6 mmoles) of sodium 2-oxo-3-(p-methylphenyl)butanoate, and the mixture was stirred until a completely uniform solution formed. Then, 0.20 ml (2.7 mmoles) of propargyl bromide and 26 mg of triethylbenzylammonium chloride were added, and the mixture was reacted at room temperature for 12 hours. The reaction mixture was acidified with 1N hydrochloric acid and extracted with ether. The ether layer was dried over magnesium sulfate. The drying reagent was separated by filtration, and the solvent was evaporated. The resulting solid was purified to obtain 2-oxo-3-(p-methylphenyl)-5-hexynoic acid in a yield of 52 %.

Workup

  1. customformed
  2. customthe mixture was reacted at room temperature for 12 hours
  3. extractionextracted with ether
  4. dry with materialThe ether layer was dried over magnesium sulfate
  5. customThe drying reagent was separated by filtration
  6. customthe solvent was evaporated
  7. customThe resulting solid was purified

Sources & evidence

ORD record
ord-8224e732a609447398e99e14e88e8597
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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