Hydrochloric Acid → HCID 15024014, compound

HRID 1086356Notes

Reaction equation

HRID 1086356 reaction equation
[OH-].[Na+].[C:3]1([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:15](Br)[C:16]#[CH:17].Cl>>[O:14]=[C:10]([CH:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:17][C:16]#[CH:15])[C:11]([OH:13])=[O:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 997Phenylpyruvic acidHCID 7842Propargyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 15024014HCID 15024014, compoundYield 93%

Procedure

A 1N aqueous solution of sodium hydroxide (20 ml; 20 mmoles) was added to 1.64 g (10 mmoles) of phenylpyruvic acid to form a solution. Then, 1.19 g (10 mmoles) of propargyl bromide was added, and the mixture was stirred at room temperature for 13 hours. The reaction mixture was acidified with 1N hydrochloric acid and extracted with three 50 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 nearly pure 2-oxo-3-phenyl-5-hexynoic acid (1.88 g; yield 93 %).

Workup

  1. customto form a solution
  2. extractionextracted with three 50 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-dd1bba763f33478f9792b45f4c081af9
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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