Hydrochloric Acid → HCID 54106267, compound

HRID 1086366Notes

Reaction equation

HRID 1086366 reaction equation
[OH-].[Na+].[O:3]=[C:4]([CH:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl: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]([Cl:16])=[CH:14][CH:15]=1)[C:9]#[C:18][CH3:19])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 23679665HCID 23679665, compound

Product 1

HCID 54106267HCID 54106267, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 3N aqueous solution (1.0 ml) of sodium hydroxide and 5.0 ml of tetrahydrofuran were added to 0.57 g (2.4 mmoles) of sodium 2-oxo-3-(p-chlorophenyl)butanoate, and the mixture was stirred until a completely uniform solution formed. Then, 0.20 ml (2.7 mmoles) of propargyl bromide and 24 ml of triethylbenzylammonium chloride were added, and the mixture 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 oily product was purified to give the desired 2-oxo-3-(p-chlorophenyl)-hexynoic acid in a yield of 66 %.

Workup

  1. customformed
  2. customthe mixture 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 oily product was purified

Sources & evidence

ORD record
ord-fa4bd89efd814bcab546dac5d749d405
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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